Azo dyes derived from 5-membered heterocyclic amines and aromatic amine couplers containing sulfo groups, or salts thereof

ABSTRACT

Disclosed are mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing sulfoalkyl groups. These dyes impart fast violet to blue shades on polyamide fibers and have the general formula 
     
         D--N═N--Coupler 
    
     wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --Z--SO 3  M group is attached to the nitrogen thereof, the coupler ring may contain one or more substituents selected from lower alkyl, lower alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as lower alkyl, substituted lower alkyl, lower alkenyl, aryl, or cycloalkyl, M is Na + , K + , NH 4   +   or H + , and Z is a linking group such as ethylene.

This invention concerns mono azo dyes derived from diazotized 5-membered heterocyclic amines and certain aniline, 1,2,3,4-tetrahydroquinoline, and benzomorpholine couplers containing sulfoalkyl groups. These dyes are useful for dyeing synthetic fibers, cellulose acetate and wool, and particularly impart fast violet to blue shades on polyamide fibers. The dyes, in general, exhibit improved properties such as fastness to light, sublimation, ozone, oxides of nitrogen, perspiration, crock, and wash, and exhibit excellent build, pH stability, bloom resistance, depth of shade, leveling, migration, and the like.

The dyes of this invention have the general formula:

    D--N═N--Coupler

wherein D is a thiadiazol, isothiazol, pyrazol or thiophene type radical, and the Coupler is an aniline, tetrahydroquinoline, or benzomorpholine derivative wherein a --Z--SO₃ M group is attached to the nitrogen thereof, the coupler ring may contain a substituent such as lower alkyl, lower alkoxy, halogen, acylamido, alkylthio or aryloxy, the remaining hydrogen of the aniline coupler may be replaced by a substituent such as lower alkyl, substituted lower alkyl, lower alkenyl, aryl, or cycloalkyl, M is Na⁺, K⁺, NH₄ ⁺ or H⁺, and Z is a linking group such as ethylene.

More specifically, the Coupler is of the formulae ##STR1## wherein; R₁ is selected from hydrogen, lower alkyl, halogen, lower alkoxy, aryloxy, and --NHCO--R₅ or --NHSO₂ --R₅ wherein R₅ is selected from lower alkyl which may be substituted with hydroxy, lower alkoxy, cyano, aryloxy, aryl, halogen, cycloalkyl, lower alkyl carbonyloxy, or carbamoyl; hydrogen; aryl; alkoxy; alkylamino; and 2-furyl; R₂ is selected from hydrogen, aryl, cycloalkyl, and lower alkyl which may be substituted with alkoxy, alkoxyalkoxy, hydrogen, aryloxy, aryl, cycloalkyl, lower alkylcycloalkyl, furyl, acylamido, aryloxy, carbamoyl, lower alkoxy carbamoyl, lower alkyl substituted carbamoyl, cyano, alkanoyloxy, halogen, alkoxycarbonyl, succinimido, glutarimido, phthalimido, 2-pyrrolidino, sulfamoyl, lower alkyl substituted sulfamoyl, lower alkylsulfonamido, NHSO₂ -aryl, NHCOO-alkyl, NHCONH-alkyl, formamido, alkylsulfonyl, arylsulfonyl, alkylthio, arylthio or SO₃ M; R₂ may in conjunction with R₁ form a 1,2,3,4-tetrahydroquinoline or benzomorpholine derivative; n is 0, 1 or 2; M is Na⁺, K⁺, NH₄ ⁺, or H⁺ ; R₃ and R₄ are each selected from hydrogen or lower alkyl; Z is selected from straight or branched chain lower alkylene, lower alkylene substituted with aryl, aryloxy, alkoxy, halogen, aryloxy or SO₃ M, -CH₂ (CH₂)_(m) -X-CH₂ (CH₂)_(p), where m is is 1, 2, or 3, p is 0, 1, 2 or 3, and X is O, S, SO₂, ##STR2## and the various aryl groups may be substituted with lower alkyl, lower alkoxy, or halogen. The term "lower" as used through this application means 1-6 carbons.

The heterocycle D is of the formulae ##STR3## ring A may bear a substituent selected from lower alkyl, substituted lower alkyl, lower alkoxy, halogen, lower alkylsulfonyl, SO₂ O aryl, SO₂ NH₂, SO₂ NH--lower alkyl, SO₂ N--(dilower alkyl), arylsulfonyl, substituted SO₂ NH--lower alkyl, acylamido, aryl, arylthio, alkenylthio, cyclohexylthio, thiocyano, cyclohexylsulfonyl, lower alkylthio, substituted lower alkylthio and cyclohexyl;

ring B may bear a substituent selected from lower alkyl, substituted lower alkyl, aryl, lower alkylthio, cyclohexylthio, substituted lower alkylthio and lower alkylsulfonyl;

ring C may bear one or two substituents selected from alkyl, substituted lower alkyl, halogen, cyano, carbamoyl, CONH--lower alkyl, substituted CONH--lower alkyl, lower alkoxycarbonyl, lower alkylthio, substituted lower alkylthio, alkenylthio, arylthio, cyclohexylthio, S-heterocycle, aryloxy, and lower alkoxy;

ring D may bear one or two substituents selected from lower alkyl, substituted lower alkyl, lower alkoxycarbonyl, lower alkylthio, aryl, cyano, carbamoyl, lower alkyl carbamoyl, lower alkylcarbonyl, substituted lower alkyl carbamoyl, and lower alkyl sulfonyl; and

ring E may be substituted with one to three substituents selected from lower alkyl, substituted lower alkyl, cyano, lower alkoxycarbonyl, acyl, aroyl, lower alkylsulfonyl, arylsulfonyl, carbamoyl, lower alkyl carbamoyl, substituted lower alkyl carbamoyl, aryl, halogen, sulfamoyl, lower alkyl carbamoyl, substituted lower alkyl, sulfamoyl and formyl;

and wherein the various alkyl groups may bear one to three substituents selected from hydroxy, lower alkoxy, aryl, aryloxy, cyclohexyl, lower alkylcyclohexyl, acyloxy, lower alkoxy carbonyl, acylamido, lower alkylsulfonamido, succinimido, glutarimido, phthalimido, 2-pyrrolidino, cyano, carbamoyl, lower alkoxy-alkoxy, lower alkylthio, halogen, arylthio, lower alkylsulfonyl and arylsulfonyl;

and wherein the various aryl groups may be substituted with one to three substituents selected from lower alkyl, lower alkoxy, halogen, lower alkoxy carbonyl, lower alkyl sulfonyl, and lower alkylthio.

The following couplers are particularly valuable in the practice of this invention. ##STR4##

The intermedite couplers containing a sulfoethyl group may be prepared in the best purity by reacting aromatic amines such as anilines, tetrahydroquinolines and benzomorpholines with vinylsulfonyl fluoride, followed by basic hydrolysis. Typical is the reaction ##STR5##

Other general methods useful for preparing these couplers containing sulfo groups are given by R. B. Wagner and H. D. Zook, "Synthetic Organic ChemistryS", John Wiley & Sons, Inc., New York, 1953, pp. 812-819. Exemplary are the methods (I) oxidation of mercaptans; (II) alkylation of alkali sulfite; and (III) addition of bisulfites to unsaturated compounds, as follows: ##STR6##

The following coupler intermediates, bearing one or more hydrogens, are typical of those appropriate for reacting with sodium sulfite according to above method II. ##STR7##

The halogen containing couplers are in general prepared by reacting the corresponding known hydroxy compounds with POCl₃, SOCl₂, POBr₃, PBr₃, and the like by methods well known in the art. The tetrahydroquinolines and benzomorpholines are similarly prepared.

The following coupler intermediates are typical of those containing vinyl groups capable of being reacted with sodium bisulfide method III as disclosed, for example, in U.S. Pat. Nos. 3,369,013; 3,415,810; and 3,472,833. ##STR8##

Intermediates containing the acrylamide and vinylsulfonamido groups can be prepared by reacting the corresponding amino compound with acryloyl chloride and vinylsulfonyl fluoride, respectively by methods well known in the art.

Preparation of N-(2-Fluorosulfonylethyl)-N-ethyl-m-toluidine

N-Ethyl-m-toluidine (66.5 g) (0.05 m) is dissolved in isopropyl alcohol (75 ml) and vinylsulfonyl fluoride (55 g 0.5) is added dropwise over 1.25 hr. The reaction exotherms to 38° C. and the reaction mixture is stirred for 1 hr. at ambient temperature and drowned into 500 ml of ice and water. The product is collected by filtration, washed with water, and dried in air. The product melts at 32°-34° C.

Preparation of N-(2-Potassiousulfoethyl)-N-ethyl-m-toluidine

N-(2-Fluorosulfonylethyl)-N-ethyl-m-toluidine (24.5 g., 0.1 m) is stirred in water (200 ml) and potassium hydroxide (10 g) for 1-3 hours at room temperature or until thin-layer chromatography shows the reaction to be complete. The product is not isolated but is used as an aqueous solution in the coupling reaction.

Preparation of N-(2-Fluorosulfonylethyl)-N-ethylaniline

N-Ethylaniline (48.4 g 0.4 m), triethylamine (40.4 g 0.4 m) and benzene (100 ml) are stirred together at room temperature and 2-chloroethanesulfonyl fluoride (58.6 g, 0.4 m) is added dropwise. The reaction mixture is heated at reflux for 1.5 hr. after the addition is completed. The reaction mixture is cooled and filtered to remove any insoluble salts, and the benzene is removed by distillation. The crude product is drowned into hexane (150 ml) and purified by filtration and washing with hexane. The product melts at 48°-50° C.

Preparation of N-(2-Potassiosulfoethyl)-N-ethylaniline

N-(2-Fluorosulfonylethyl)-N-ethylaniline (22.8 g, 0.1 n) is stirred in water (200 ml) and potassium hydroxide (10 g) for 1-3 hrs. or until thin-layer chromatography shows reaction to be complete. The product is not isolated but is used as an aqueous solution in the coupling reaction.

Preparation of N-(2-Fluorosulfonylethyl)-2-methyl-5-acetamidonaniline

2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45° C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154°-155° C.

Preparation of N-(2-Potassiosulfoethyl)-2-methyl-5-acetamido aniline

N-(2-Fluorosulfonylethyl-2-methyl-5-acetamidoaniline (13.7 g, 0.05 m) is stirred with water (100 ml.) and potassium hydroxide (5.0 g) at room temperature for 2 hrs. when thin-layer chromatography shows reaction to be complete. The aqueous solution is used in the coupling reaction without further isolation.

Preparation of N-(2-Fluorosulfonylethyl)-2-methoxy-5-methylaniline

2-Methoxy-5-methylaniline (34.3 g 0.25 m) is dissolved in N,N-dimethylformamide (50 ml). Vinylsulfonyl fluoride (28.0 g, 0.26 m) is added dropwise at 20°-30° C. After the addition is complete the reaction mixture is allowed to stir at ambient temperature for 1 hr. The reaction is drowned into water (400 ml)., the product collected by filtration, washed with water and air dried. The product melts at 56°-58° C. The corresponding N-(2-potassiosulfoethyl)-2-methoxy-5-methylaniline is prepared therefrom by the above technique using KOH.

Preparation of N-(2-Fluorosulfonylethyl)-2,2,4,7-tetramethyl 1,2,3,4-tetrahydroquinoline

2,2,4,7-Tetramethyl-1,2,3,4-tetrahydroquinoline (94.5 g, 0.5 m) is dissolved in acetic acid (200 ml). The reaction is heated to 50° C. and vinylsulfonylfluoride (44.0 g, 0.5 m) added over 30 min. at 48°-50° C. The reaction is then stirred and heated for 2.5 hr. at 50°-55° C. Thin-layer chromatography shows the reaction to be complete. The reaction mixture is drowned into water (1200 ml), the product collected by filtration, washed with water and air dried. The product melts at 67°-69° C.

N-(2-fluorosulfonylethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline and N-(2-fluorosulfonylethyl 2,7-dimethyl-1,2,3,4-tetrahydroquinoline is prepared in same manner.

Preparation of N-(2-Sodiosulfoethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline

N-(2-fluorosulfonylethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline (12.0 g, 0.04 m) is stirred with water (100 ml) and sodium hydroxide (5.0 g(, warmed to 50° C. for 30 min., allowed to come to room temperature and stirred for 1.5 hr. Thin layer chromatography shows the reaction to be complete. The aqueous solution is not isolated but is used in the coupling reaction.

The same process is used to prepare N-(2-potassiosulfoethyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline and N-(2-potassiosulfoethyl)-2,7-dimethyl-1,2,3,4-tetrahydroquinoline using KOH as the base.

Preparation of N-(2-Flourosulfonylethyl)-3,6-dimethyl-2,3-dihydro-1,4-benzoxazine

3,6-Dimethyl-2,3-dihydro-1,4-benzoxazine (16.3 g, 0.1 m) is dissolved in acetic acid (40 ml) at ambient temperature and vinylsulfonylfluoride (11 g., 0.1 m) is added dropwise at 25°-35° C. After stirring for 1.5 hr., the reaction is complete. The reaction is drowned into water (400 ml). The dark oil which separates is extracted with hexane (1200 ml) and the hexane solution dried over sodium sulfate. The sodium sulfate is removed and the hexane distilled off to yield 23.3 g. of oily product. The N-2(Potassiosulfoethyl)-3,6-dimethyl-2,3-dihydro-1,4-benzoxazine is prepared as above using KOH.

Preparation of N-(2-Fluorosulfonylethyl)-N-ethyl-m-acetamidoaniline

N-ethyl-m-acetamidoaniline (178.0 g, 1.0 m is dissolved in isopropyl alcohol (450 ml) and vinylsulfonylfluoride (110 g, 1.0 m) is added dropwise allowing temperature to rise to 40° C. The reaction is stirred for 2.5 hrs., the product collected by filtration, washed with cold ethanol and air dried.

Preparation of N-(2-Sodiosulfoethyl)-sulfonylethyl-N-ethyl-m-toluidine

N-(2-vinylsulfonylethyl-N-ethyl-m-toluidine (25.3 g, 0.1 m) in water solution (100 ml) is stirred with sodium bisulfite (11.0 g, 0.1 m). The reaction is heated to reflux and held for 15 min. The clear solution is drowned into ethanol (200 ml) and allowed to cool. The white solid is collected by filtration, air dried and melts at 237°-240° C.

Vinylsulfonyl fluoride may be prepared according to U.S. Pat. Nos. 2,653,973 and 2,884,452 and L. Z. Soboronskii, et. al., J. Gen. Chem. U.S.S.R., 28, 1913 (1958). The amine diazo precursors can be prepared from readily available intermediates by well known techniques.

This invention will be further illustrated by the following examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.

EXAMPLES 1-10 Diazotization and Coupling of 2-Amino-5-ethylthio-1,3,4-thiadiazole

Sodium nitrite (3.6 g.) is added portionwise to 25 ml of concentrated H₂ SO₄. The solution is cooled and 100 ml of 1:5 acid (1 part propionic: 1 part acetic) is added below 15° C. The mixture is cooled and 8.05 g. (0.05 m) of 2-amino-5-ethylthio-1,3,4-thiadiazole is added below 10° C. After stirring at 0°-5° C. for 2 hrs., a 0.005 m aliquot of the diazonium salts is added to 0.005 m of the following couplers in water or dilute sulfuric acid, keeping the temperature below 5° C.

N-Ethyl-N-2-sulfoethyl-m-toluidine, K salt (Example 1)

N-Ethyl-N-sulfoethyl-2-methoxy-5-methylaniline, K salt (Example 2).

5-Acetamido-2-methyl-N-sulfoethyl aniline, K salt (Example 3).

N-(2-Sulfoethyl)-1,2,3,4-tetrahydro-2,2,4,7-tetramethyl quinoline, K salt (Example 4)

N-(2-Sulfoethyl)-1,2,3,4-tetrahydro-2,2,4-trimethyl quinoline, K salt (Example 5)

2,7-Dimethyl-N-(2-sulfoethyl)-1,2,3,4-tetrahydroquinoline, K salt (Example 6)

8-Methoxy-5-methyl-N-(2-sulfoethyl)-1,2,3,4-tetrahydro quinoline, K salt (Example 7)

2,7-Dimethyl-N-(2,3-disulfopropyl)-1,2,3,4-tetrahydro quinoline, K salt (Example 8)

2,3-Dihydro-3,6-dimethyl-N-(2-sulfoethyl)-1,4-benzoxazine, K salt (Example 9)

2,3-Dihydro-3-methyl-7-methoxy-N-(2-sulfoethyl)-1,4-benzoxazine, K salt (Example 10)

The mineral acid is neutralized with potassium acetate and the coupling mixture allowed to stand for 1 hr. Water is added to make a total volume of 200-300 ml. and the dyes are collected by filtration, washed with water, and dried in air.

The dyes usually contain about an equal weight of dye and potassium sulfate as they are isolated and are used for dying polyamide fibers red shades without further purification. The dyes in the following tables are prepared in a similar manner. Neutralization using sodium hydroxide and ammonium hydroxide results in the corresponding sodium and ammonium salts, respectively.

                                      TABLE 1                                      __________________________________________________________________________      ##STR9##                                                                      R           (R.sub.1).sub.m                                                                            R.sub.2        Z                   M                   __________________________________________________________________________     5-CH.sub.3  2-CH.sub.3  H              CH.sub.2 CH.sub.2   K.sup.+             5-CH.sub.2 CH.sub.3                                                                        2-Cl        "              "                   "                   5-CH.sub.2 CH(CH.sub.3)                                                                    2,5-di-Cl   "              "                   "                   5-C.sub.6 H.sub.5                                                                          2,5-di-CH.sub.3                                                                            "              "                   "                   5-C.sub.6 H.sub.11                                                                         2,5-di-OCH.sub.3                                                                           "              "                   "                   5-C.sub.6 H.sub.4p-Cl                                                                      3-OCH.sub.3 C.sub.2 H.sub.5                                                                               "                   "                   5-C.sub.6 H.sub.4o-CH.sub.3                                                                2-OCH.sub.3, 5-NHCOCH.sub.3                                                                H              "                   "                   5-C.sub.6 H.sub.4m-OCH.sub.3                                                               2-CH.sub.3, 3-Cl                                                                           "              "                   "                   5-SCH.sub.3 2-OCH.sub.3, 5-Cl                                                                          "              "                   "                   "           3-NHCOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                               "                   "                   "           3-NHCOC.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 OCH.sub.3                                                                     "                   "                   "           3-NHCOCH.sub.2 OH                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                      "                   "                   "           3-NHCOCH.sub.2 OCH.sub.3                                                                   C.sub.6 H.sub.11                                                                              "                   "                   "           3-NHCOC.sub.6 H.sub.5                                                                      CH.sub.2 C.sub.6 H.sub.11                                                                     "                   "                   "           3-NHCOOC.sub.2 H.sub.5                                                                     CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                            "                   "                   "           3-NHCONHC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OH                                                                          "                   "                   5-OC.sub.2 H.sub.5                                                                         3-NHCOC.sub.6 H.sub.11                                                                     CH.sub.2 CH(CH.sub.3).sub.2                                                                   "                   "                   5-SC.sub.2 H.sub.5                                                                         3-NHCOCH.sub.2 CN                                                                          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           "                   "                   "           3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 "                   "                   "           3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                             CH.sub.2 CH.sub.2 CONH.sub.2                                                                  "                   "                   "           3-CH.sub. 3 CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                "                   "                   "           "           CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                         "                   "                   "           "           CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                           "                   "                   "           "           CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                  "                   "                   5-Cl        "           CH.sub.2 CH.sub.2 SCH.sub.3                                                                   "                   "                   5-SO.sub.2 CH.sub.3                                                                        "                                                                                           ##STR10##     CH.sub.2 CH.sub.2 CH.sub.2                                                                         Na.sup.+            5-OC.sub.4 H.sub.9n                                                                        "                                                                                           ##STR11##     "                   "                   5-SCH.sub.2 CH.sub.2 OH                                                                    3-OC.sub.6 H.sub.5                                                                          ##STR12##     "                   NH.sub.4.sup.+                                                                 3                   5-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                           3-CH.sub.3  C.sub.6 H.sub.5                                                                               CH.sub.2 CH.sub.2   Na.sup.+             ##STR13##  "                                                                                           ##STR14##     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)            "                   5-SCH.sub.2 SC.sub.6 H.sub.5                                                               "           CH.sub.2 CH.sub.2 COOCH.sub.3                                                                 CH.sub.2 CH(C.sub.6 H.sub.5)                                                                       "                   5-SO.sub.2 CH.sub.3                                                                        "           CH.sub.2 CH.sub.2 CN                                                                          CH.sub.2 CH(CH.sub.3)                                                                              "                   5-SO.sub.2 NH.sub.2                                                                        "           C.sub.2 H.sub.5                                                                               CH.sub.2 CH(OH)CH.sub.2                                                                            "                   5-SO.sub.2 NHC.sub.2 H.sub.5                                                               2-CH.sub.3 S                                                                               H              CH.sub.2 CH.sub.2 CH.sub.2                                                                         "H.sub.2            5-SCN       3-CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                                     CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                   "                   5-SO.sub.2 N(CH.sub.3).sub.2                                                               "           CH.sub.2 CH(OH)CH.sub.2 Cl                                                                    CH.sub.2 CH.sub.2   "                   5-SO.sub.3 C.sub.6 H.sub.5                                                                 2-OCH.sub.3, 5-CH.sub.3                                                                    C.sub.2 H.sub.5                                                                               "                   "                   5-SCH.sub.2 CHCH.sub.2                                                                     "           H              CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2            "                   5-SCH.sub.2 CH.sub.2 OCH.sub.3                                                             "           H              "                   "                    ##STR15##  "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2   K.sup.+             5-SC.sub.6 H.sub.11                                                                        3-CH.sub.3  C.sub.2 H.sub.5                                                                               CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2            "                   5-SC.sub.6 H.sub.5                                                                         "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                         "                   5-SO.sub.2 C.sub.6 H.sub.5                                                                 "           "              CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                                         "H.sub.2            5-I         "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2 "                   5-Br        "           "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s                                            ub.2 CH.sub.2       "                    ##STR16##  "           "              CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4             "                   5-SCH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                   "           "              CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                     "                   5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3                                                          "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2 CH.sub.2                                                                  "                   5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                      "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                       "                   5-SCH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                       "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                                         "H.sub.2            5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2 CH.sub.2                                                                 "                   5-SO.sub.2 C.sub.6 H.sub.11                                                                "           "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s                                            ub.2 CH.sub.2       "                   5-CH.sub. 3 "           "              CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                    "                   "           "           "              CH.sub.2 CH(Cl)CH.sub.2                                                                            "                   "           "           "              CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4             "                   5-NHCOCH.sub.3                                                                             "           "              CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2            "                   "           "           "              CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2            "                   __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR17##                                                                     R           (R.sub.1).sub.m                                                                             R.sub.3                                                                           R.sub.4                                                                              Z                M                           __________________________________________________________________________     H           H            CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               K.sup.+                     "           7-CH.sub.3   "  "     "                "                           "           7-OCH.sub.3  "  "     "                "                           5-CH.sub.3  7-Cl         "  "     "                "                           5-CH.sub.2 CH.sub.3                                                                        5-CH.sub.3, 8-OCH.sub.3                                                                     "  "     "                "                           5-CH(CH.sub.3).sub.2                                                                       5,8-di-OCH.sub.3                                                                            "  "     "                "                           5-CH.sub.2 CH(CH.sub.3).sub.2                                                              5,8-di-CH.sub.3                                                                             "  "     "                "                           5-C.sub.6 H.sub.5                                                                          5-Cl, 8-OCH.sub.3                                                                           "  "     "                "                           5-C.sub.6 H.sub.11                                                                         8-OCH.sub.3  "  "     "                "                           5-C.sub.6 H.sub.4o-Cl                                                                      8-OC.sub.2 H.sub.5                                                                          H  H     "                "                           5-C.sub.6 H.sub.4n-CH.sub.3                                                                7-CH.sub.3   "  "     "                "                           5-C.sub.6 H.sub.4p-OCH.sub.3                                                               7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                             "                Na.sup.+                    5-OC.sub.2 H.sub.5                                                                         7-NHCOH      "  "     "                "                           "           7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "     "                "                           "           7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                   "                "                           "           7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "     "                "                           "           7-NHCOCH.sub.2 Cl                                                                           "  "     "                "                           "           7-NHCOC.sub.6 H.sub.5                                                                       "  "     "                "                           "           7-NHCOC.sub.6 H.sub.11                                                                      CH.sub.3                                                                          CH.sub.3                                                                             "                "                           5-Cl        7-NHCONHC.sub.2 H.sub.5                                                                     "  "     "                "                           "           7-NHSO.sub.2 CH.sub.3                                                                       "  "     "                "                           "           7-NHCOCH.sub.2 CN                                                                           "  "     "                "                           "           7-NHCOCH.sub.2 OH                                                                           "  "     "                "                           5-I         7-NHCOOC.sub.2 H.sub.5                                                                      "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                      "                           5-Br                                                                                        ##STR18##   "  "     "                "                           5-SO.sub.2 CH.sub.3                                                                        8-OC.sub.4 H.sub.9n                                                                         H  CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               "                           5-SO.sub.2 NH.sub.2                                                                        7-CH.sub.3   CH.sub.3                                                                          H     "                "                           5-SO.sub.2 N(CH.sub.3).sub.2                                                                ##STR19##   "  CH.sub.3                                                                             "                "                           5-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                        7-OC.sub.2 H.sub.5                                                                          "  "     "                "                           8-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3                                                     7-OC.sub.4 H.sub.9n                                                                         "  "     "                "                           5-SO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                              7-CH.sub.3   "  H     "                "                           5-SC.sub.6 H.sub.5                                                                         "            "  "     "                "                           5-SC.sub.6 H.sub.11                                                                        "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                             "                           5-SO.sub.2 C.sub.6 H.sub.5                                                                 "            "  "     CH.sub.2 CH.sub.2                                                                               "                           5-SO.sub.3 C.sub.6 H.sub.5                                                                 "            "  "     "                "                           5-SCH.sub.2 CH.sub.2 OH                                                                    "            "  "     "                "                           5-SCH.sub.2 CHCH.sub.3                                                                     "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2         K.sup.+                     5-SCH.sub.2 COOC.sub.2 H.sub.5                                                             "            "  "     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                            "                           5-SCH.sub.2 C.sub.6 H.sub.5                                                                "            "  "     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                            "                           5-SCH.sub.2 C.sub.6 H.sub.11                                                               "            "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                           5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      "            "  "      CH.sub.2 CH(CH.sub.3)                                                                          "                           5-SCN       "            "  "     CH.sub.2 CH(OH)CH.sub.2                                                                         "                           5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3                                                          "            "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                         "                            ##STR20##  "            "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2 CH.sub.3)                                                        "                           5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                      "            "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5)                                                          "                           5-SCH.sub.2 CH.sub.3                                                                       "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH                                       .sub.2 CH.sub.2  "                           "           "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2                                          CH.sub.2 CH.sub.2                                                                               "                           "           "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2         "                           "           "            "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                           "           "            "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                                 "H.sub.2                    "           "            "  "     CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2                                                          "                           "           "            "  "     CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4                                                           "                           5-SCH.sub.3 "            "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                                 ".sub.4                     "           "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                           "           "            "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2                                        CH.sub.2         "                           "           "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                           5-NHCOCH.sub.3                                                                             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH                                       .sub.2 CH.sub.2  "                           __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR21##                                                                     R             (R.sub.1).sub.m                                                                              R.sub.3                                                                           Z                     M                         __________________________________________________________________________     H             6-CH.sub.3    H  CH.sub.2 CH.sub.2     K.sup.+                   "             H             H  "                     "                         "             "             CH.sub.3                                                                          "                     "                         5-CH.sub.3    6-CH.sub.3    "  "                     "                         5-CH(CH.sub.3).sub.2                                                                         "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  "                         5-CH.sub.2 CH(CH.sub.3).sub.2                                                                6-OCH.sub.3   "  "                     "                         5-C.sub.6 H.sub.5                                                                            "             "  CH.sub.2 CH.sub.2     "                         5-C.sub.6 H.sub.4p-Cl                                                                        6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                 "                         5-C.sub.6 H.sub.4p-OCH.sub.3                                                                 "             "  CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2              "                         5-C.sub.6 H.sub.4n-CH.sub.3                                                                  "             "  CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                 "                         5-OC.sub.2 H.sub.5                                                                           "             "  CH.sub.2 CH(CH.sub.3) "                         5-OCH(CH.sub.3).sub.2                                                                        "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                         "                         5-C.sub.6 H.sub.11                                                                           6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2     "                         5-SCN         6-NHCOCH.sub.3                                                                               "  "                     Na.sup.+                  5-SCH.sub.3   6-NHCOH       "  "                     "                         5-SCH.sub.2 CH(CH.sub.3).sub.2                                                               6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                     "                         5-SCH.sub.2 CHCH.sub.2                                                                       6-NHCOCH.sub.2 Cl                                                                            "  "                     "                         5-SC.sub.6 H.sub.11                                                                          6-NHCOCH.sub.2 CN                                                                            "  "                     "                         5-SC.sub.6 H.sub.5                                                                           6-NHCOCH.sub.2 CONH.sub.2                                                                    "  "                     "                         5-SCH.sub.2 C.sub.6 H.sub.5                                                                  6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                     "                         5-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                        6-NHCOOC.sub.2 H.sub.5                                                                       "  "                     "                         5-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        6-NHCONHC.sub.2 H.sub.5                                                                      "  "                     "                         5-SCH.sub.2 CH.sub.2 OH                                                                      6-NHCOC.sub.6 H.sub.5                                                                        "  "                     "                         5-SCH.sub.2 CH.sub.2 Cl                                                                      6-NHCOC.sub.6 H.sub.11                                                                       "  "                     "                         5-SCH.sub.2 COOC.sub.2 H.sub.5                                                               6-NHSO.sub.2 CH.sub.3                                                                        "  "                     "                         5-SCH.sub.2 CH.sub.2 OCOCH.sub.3                                                             6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                     "                         5-SCH.sub.2 C.sub.6 H.sub.11                                                                  ##STR22##    "  "                     "                         5-SO.sub.2 CH.sub.3                                                                          6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                     "                         5-SO.sub.2 C.sub.4 H.sub.9n                                                                  6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                         5-SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "             "  CH.sub.2 CH.sub.2     "                         5-SO.sub.2 C.sub.6 H.sub.5                                                                   "             "  "                     "                         5-SO.sub.2 C.sub.6 H.sub.11                                                                  "             "  "                     "                         5-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                          "             "  "                     "                         5-SO.sub.2 CH.sub.2 CH.sub.2 OH                                                              "             "  "                     "                          ##STR23##    "             "  "                     "                         5-SCH.sub.2 CH.sub.2 NHCOCH.sub.3                                                            "             "  "                     "                          ##STR24##    "             H  CH.sub.2 CH(CH.sub.3) "                         5-SO.sub.2 NH.sub.2                                                                          "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.su                                    b.2 CH.sub.2          K.sup.+                   5-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3                                                       "             "  CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2              "                         5-SO.sub.2 NH(CH.sub.3).sub.2                                                                "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.su                                    b.2 CH.sub.2 CH.sub.2 "                         5-SO.sub. 2 NHC.sub.2 H.sub.5                                                                "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                            "                         5-SO.sub.2 NHC.sub.6 H.sub.11                                                                "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                         5-SO.sub.3 C.sub.6 H.sub.5                                                                   "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2                                                                "                         5-SO.sub.2 NHC.sub.6 H.sub.5                                                                 "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2                                                                  "                         5-NHCOCH.sub.3                                                                               "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                         5-SC.sub.2 H.sub.5                                                                           "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                              "                         "             "             "  CH.sub.2 CH(OH)CH.sub.2                                                                              "                         "             "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                      "                         "             "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6                                                                        ".sub.5)                  "             "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                     "                         "             "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                       "                         "             "             "  CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4                                                                "                         "             "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2                                                             "                         "             "             "  CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2                                                               "                         "             "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2                                                            "                         "             "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2                                        CH.sub.2              "                         "             "             "  CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.su                                    b.2 CH.sub.2          "                         __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR25##                                                                     R           (R.sub.1).sub.m                                                                            R.sub.2        Z                   M                   __________________________________________________________________________     3-CH.sub.3  2-CH.sub.3  H              CH.sub.2 CH.sub.2   K.sup.+             "           2-Cl        "              "                   "                   "           2,5-di-Cl   "              "                   "                   "           2,5-di-CH.sub.3                                                                            "              "                   "                   "           2,5-di-OCH.sub.3                                                                           "              "                   "                   "           3-OCH.sub.3 C.sub.2 H.sub.5                                                                               "                   "                   "           2-OCH.sub.3, 5-NHCOCH.sub.3                                                                H              "                   "                   3-SCH.sub.3 2-CH.sub.3, 3-Cl                                                                           "              "                   "                   3-C.sub.6 H.sub.5                                                                          2-OCH.sub.3, 5-Cl                                                                          "              "                   "                   3-C.sub.6 H.sub.4 p-Cl                                                                     3-NHCOCH.sub.3                                                                             C.sub.2 H.sub.5                                                                               "                   "                   3-C.sub.6 H.sub.4o-CN                                                                      3-NHCOC.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 OCH.sub.3                                                                     "                   "                   "           3-NHCOCH.sub.2 OH                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                      "                   "                   "           3-NHCOCH.sub.2 OCH.sub.3                                                                   C.sub.6 H.sub.11                                                                              "                   "                   "           3-NHCOC.sub.6 H.sub.5                                                                      CH.sub.2 C.sub.6 H.sub.11                                                                     "                   "                   "           3-NHCOOC.sub.2 H.sub.5                                                                     CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                            "                   "                   "           3-NHCONHC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OH                                                                          "                   "                   "           3-NHCOC.sub.6 H.sub.11                                                                     CH.sub.2 CH(CH.sub.3).sub.2                                                                   "                   "                   3-C.sub.6 H.sub.5                                                                          3-NHCOCH.sub.2 CN                                                                          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           "                   "                   "           3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 "                   "                   "           3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                             CH.sub.2 CH.sub.2 CONH.sub.2                                                                  "                   "                   "           3-CH.sub.3  CH.sub.2 CH.sub.2 NHCOCH.sub. 3                                                               "                   "                   "           "           CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                         "                   "                   3-C.sub.6 H.sub.4p-CH.sub.2                                                                "           CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                           "                   "                   3-C.sub.6 H.sub.5                                                                          "           CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                  "                   "                   "           "           CH.sub.2 CH.sub.2 SCH.sub.3                                                                   "                   "                   "           "                                                                                           ##STR26##     CH.sub.2 CH.sub.2 CH.sub.2                                                                         Na.sup.+            "           "                                                                                           ##STR27##     "                   "                   "           3-OC.sub.6 H.sub.5                                                                          ##STR28##     "                   NH.sub.4.sup.+      "           3-CH.sub.3  C.sub.6 H.sub.5                                                                               CH.sub. 2 CH.sub.2  Na.sup.+            "           "                                                                                           ##STR29##     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)            "                   3-SO.sub.2 CH.sub.3                                                                        "           CH.sub.2 CH.sub.2 COOCH.sub.3                                                                 CH.sub.2 CH(C.sub.6 H.sub.5)                                                                       "                   3-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                           "           CH.sub.2 CH.sub.2 CN                                                                          CH.sub.2 CH(CH.sub.3)                                                                              "                   3-SCH.sub.2 C.sub.6 H.sub.5                                                                "           C.sub.2 H.sub.5                                                                               CH.sub.2 CH(OH)CH.sub.2                                                                            "                   3-SCH.sub.2 CH.sub.2 OCH.sub.3                                                             2-CH.sub.3 S                                                                               H              CH.sub.2 CH.sub.2 CH.sub.2                                                                         "H.sub.2            3-SC.sub.6 H.sub.11                                                                        3-CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                                     CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                   "                   3-SC.sub.2 H.sub.5                                                                         "           CH.sub.2 CH(OH)CH.sub.2 Cl                                                                    CH.sub.2 CH.sub.2   "                   "           2-OCH.sub.3, 5-CH.sub.3                                                                    C.sub.2 H.sub.5                                                                               "                   "                   "           "           H              CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2            "                   "           "           H              "                   "                   "           "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2   K.sup.+             3-SCH.sub.2 COOCH.sub.3                                                                    3-CH.sub.3  C.sub.2 H.sub.5                                                                               CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2            "                   "           "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                         "                   "           "           "              CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                                         "H.sub.2            "           "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2 "                   3-SCH.sub.3 "           "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s                                            ub.2 CH.sub.2       "                   "           "           "              CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4             "                   "           "           "              CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                     "                   "           "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2 CH.sub.2                                                                  "                   3-SCH.sub.2 CH(CH.sub.3).sub.2                                                             "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                       "                   "           "           "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                                         "H.sub.2            "           "           "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2 CH.sub.2                                                                 "                   "           "           "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s                                            ub.2 CH.sub.2       "                   "           "           "              CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                    "                   "           "           "              CH.sub.2 CH(Cl)CH.sub.2                                                                            "                   "           "           "              CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4             "                   "           "           "              CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2            "                   "           "           "              CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2            "                   __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________      ##STR30##                                                                     R             (R.sub.1).sub.m                                                                             R.sub.3                                                                           R.sub.4                                                                              Z                 M                        __________________________________________________________________________     3-CH.sub.3    H            CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2 K.sup.+                  "             7-CH.sub.3   "  "     "                 "                        "             7-OCH.sub.3  "  "     "                 "                        "             7-Cl         "  "     "                 "                        "             5-CH.sub.3, 8-OCH.sub.3                                                                     "  "     "                 "                        "             5,8-di-OCH.sub.3                                                                            "  "     "                 "                        "             5,8-di-CH.sub.3                                                                             "  "     "                 "                        "             5-Cl, 8-OCH.sub.3                                                                           "  "     "                 "                        "             8-OCH.sub.3  "  "     "                 "                        "             8-OC.sub.2 H.sub.5                                                                          H  H     "                 "                        3-SCH.sub.3   7-CH.sub.3   "  "     "                 "                        3-C.sub.6 H.sub.5                                                                            7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                             "                 Na.sup.+                 "             7-NHCOH      "  "     "                 "                        "             7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "     "                 "                        "             7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                   "                 "                        "             7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "     "                 "                        "             7-NHCOCH.sub.2 Cl                                                                           "  "     "                 "                        "             7-NHCOC.sub.6 H.sub.5                                                                       "  "     "                 "                        "             7-NHCOC.sub.6 H.sub.11                                                                      CH.sub.3                                                                          CH.sub.3                                                                             "                 "                        "             7-NHCONHC.sub.2 H.sub.5                                                                     "  "     "                 "                        "             7-NHSO.sub.2 CH.sub.3                                                                       "  "     "                 "                        "             7-NHCOCH.sub.2 CN                                                                           "  "     "                 "                        C.sub.6 H.sub.4o-CN                                                                          7-NHCOCH.sub.2 OH                                                                           "  "     "                 "                        "             7-NHCOOC.sub.2 H.sub.5                                                                      "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                       "                                       ##STR31##   "  "     "                 "                        "             8-OC.sub.4 H.sub.9n                                                                         H  CH.sub.3                                                                             CH.sub.2 CH.sub.2 "                        3-C.sub.6 H.sub.4p-CH.sub.3                                                                  7-CH.sub.3   CH.sub.3                                                                          H     "                 "                        3-C.sub.6 H.sub.4o-Cl                                                                         ##STR32##   "  CH.sub.3                                                                             "                 "                        3-SO.sub.2 CH.sub.3                                                                          7-OC.sub.2 H.sub.5                                                                          "  "     "                 "                        3-SC.sub.6 H.sub.11                                                                          7-OC.sub.4 H.sub.9n                                                                         "  "     "                 "                        3-SCH.sub.2 CH.sub.2 OCH.sub.3                                                               7-CH.sub.3   "  H     "                 "                        3-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                             "            "  "     "                 "                        3-SCH.sub.2 C.sub.6 H.sub.5                                                                  "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                              "                        3-CH.sub.2 CH.sub.3                                                                          "            "  "     CH.sub.2 CH.sub.2 "                        3-SCH.sub.2 COOCH.sub.3                                                                      "            "  "     "                 "                        3-SCH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                                                      "            "  "     "                 "                        3-SCH.sub.2 CH.sub.2 COOCH(CH.sub.3).sub.2                                                   "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2          K.sup.+                  3-SO.sub.2 C.sub.4 H.sub.9n                                                                  "            "  "     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                             "                        3-SCH.sub.2 CH.sub.2 CONHC.sub.4 H.sub.9n                                                    "            "  "     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                             "                        3-SCH.sub.3   "            "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                     "                        "             "            "  "     CH.sub.2 CH(CH.sub.3)                                                                            "                        3-SC.sub.2 H.sub.5                                                                           "            "  "     CH.sub.2 CH(OH)CH.sub.2                                                                          "                        "             "            "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                          "                        "             "            "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)         "                        "             "            "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                                    ".sub.5)                 "             "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)                                         CH.sub.2 CH.sub.2 "                        "             "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 NHSO.sub.2                                          CH.sub.2 CH.sub.2 "                        "             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2          "                        "             "            "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                   "                        "             "            "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2          "                        "             "            "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                                    "H.sub.2                 "             "            "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                                    ".sub.4                  "             "            "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4           "                        "             "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                        "                        "             "            "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.                                         2 CH.sub.2        "                        "             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                        "                        "             "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)                                         CH.sub.2 CH.sub.2 "                        __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________      ##STR33##                                                                     R             (R.sub.1).sub.m                                                                              R.sub.3                                                                           Z                      M                        __________________________________________________________________________     3-CH.sub.3    6-CH.sub.3    H  CH.sub.2 CH.sub.2      K.sup.+                  "             H             H  "                      "                        "             "             CH.sub.3                                                                          "                      "                        "             6-CH.sub.3    "  "                      "                        "             "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                   "                        "             6-OCH.sub.3   "  "                      "                        3-SCH.sub.3   "             "  CH.sub.2 CH.sub.2      "                        3-CH.sub.2 CH.sub.3                                                                          6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                  "                        3-SCH.sub.2 CH.sub.2 OCH.sub.3                                                               "             "  CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2               "                        3-SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        "             "  CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                  "                        3-SCH.sub.2 CH.sub.2 COOCH.sub.3                                                             "             "  CH.sub.2 CH(CH.sub.3)  "                        3-SCH.sub.2 COOCH.sub.2 CH.sub.3                                                             "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                          "                        3-SCH.sub.2 C.sub.6 H.sub.5                                                                  6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2      "                        3-SC.sub.6 H.sub.11                                                                          6-NHCOCH.sub.3                                                                               "  "                      Na.sup.+                 3-SCH.sub.3   6-NHCOH       "  "                      "                        "             6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                      "                        "             6-NHCOCH.sub.2 Cl                                                                            "  "                      "                        "             6-NHCOCH.sub.2 CN                                                                            "  "                      "                        "             6-NHCOCH.sub.2 CONH.sub.2                                                                    "  "                      "                        "             6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                      "                        3-SO.sub.2 CH.sub.3                                                                          6-NHCOOC.sub.2 H.sub.5                                                                       "  "                      "                        3-SO.sub.2 C.sub.4 H.sub.9n                                                                  6-NHCONHC.sub.2 H.sub.5                                                                      "  "                      "                        3-C.sub.6 H.sub.5                                                                            6-NHCOC.sub.6 H.sub.5                                                                        "  "                      "                        3-C.sub.6 H.sub.4o-CN                                                                        6-NHCOC.sub.6 H.sub.11                                                                       "  "                      "                        3-C.sub.6 H.sub.4o-Cl                                                                        6-NHSO.sub.2 CH.sub.3                                                                        "  "                      "                        3-C.sub.6 H.sub.4p-CH.sub.3                                                                  6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                      "                        3-C.sub.6 H.sub.4m-CH.sub.3                                                                   ##STR34##    "  "                      "                        3-C.sub.6 H.sub.4o-CH.sub.3                                                                  6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                      "                        3-C.sub.6 H.sub.4o-CONH.sub.2                                                                6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                            "                        3-C.sub.6 H.sub.4o-CN                                                                        "             "  CH.sub.2 CH.sub. 2     "                        3-SCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                        "             "  "                      "                        3-SO.sub.2 C.sub.4 H.sub.9n                                                                  "             "  "                      "                        3-SO.sub.2 CH.sub.2 CH.sub.2 COOCH.sub.3                                                     "             "  "                      "                        3-SO.sub.2 CH.sub.2 COOCH.sub.3                                                              "             "  "                      "                        3-SO.sub.2 C.sub.6 H.sub.11                                                                  "             "  "                      "                        3-SO.sub.2 CH.sub.2 CH.sub.3                                                                 "             "  "                      "                        3-SO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "             H  CH.sub.2 CH(CH.sub.3)  "                        3-SCH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4 OH                                                  "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2 CH.sub.3)CH.su                                    b.2 CH.sub.2           K.sup.+                  3-SCH.sub.2 CH.sub.3                                                                         "             "  CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                          CH.sub.2               "                        "             "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3)CH.su                                    b.2 CH.sub.2 CH.sub.2  "                        "             "             "  CH.sub.2 CH.sub. 2 SO.sub.2 N(C.sub.6                                          H.sub.5)CH.sub.2 CH.sub.2                                                                             "                        "             "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                        "             "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2 CH.sub.2                                                                 "                        "             "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2                                                                   "                        "             "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                        3-C.sub.6 H.sub.5                                                                            "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                               "                        "             "             "  CH.sub.2 CH(OH)CH.sub.2                                                                               "                        "             "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                       "                        "             "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6 H.sub.5)                                                                "                        "             "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                      "                        "             "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                        "                        "             "             "  CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.4                                                                 "                        "             "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2 CH.sub.2                                                              "                        "             "             "  CH.sub.2 CH.sub.2 COOCH.sub.2 CH.sub.2                                                                "                        "             "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2 CH.sub.2                                                             "                        "             "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub.2                                        CH.sub.2               "                        "             "             "  CH.sub.2 CH.sub.2 N(COC.sub.6 H.sub.5)CH.su                                    b.2 CH.sub.2           "                        __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________      ##STR35##                                                                     R             (R.sub.1).sub.m                                                                           R.sub.2        Z                  M                   __________________________________________________________________________     3-CH.sub.3, 4-Br                                                                             2-CH.sub.3 H              CH.sub.2 CH.sub.2  K.sup.+             "             2-Cl       "              "                  "                   "             2,5-di-Cl  "              "                  "                   "             2,5-di-CH.sub.3                                                                           "              "                  "                   "             2,5-di-OCH.sub.3                                                                          "              "                  "                   "             3-OCH.sub.3                                                                               C.sub.2 H.sub.5                                                                               "                  "                   "             2-OCH.sub.3, 5-NHCOCH.sub.3                                                               H              "                  "                   "             2-CH.sub.3, 3-Cl                                                                          "              "                  "                   "             2-OCH.sub.3, 5-Cl                                                                         "              "                  "                   "             3-NHCOCH.sub.3                                                                            C.sub.2 H.sub. 5                                                                              "                  "                   "             3-NHCOC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 OCH.sub.3                                                                     "                  "                   "             3-NHCOCH.sub.2 OH                                                                         CH.sub.2 C.sub.6 H.sub.5                                                                      "                  "                   "             3-NHCOCH.sub.2 OCH.sub.3                                                                  C.sub.6 H.sub.11                                                                              "                  "                   "             3-NHCOC.sub.6 H.sub.5                                                                     CH.sub.2 C.sub.6 H.sub.11                                                                     "                  "                   "             3-NHCOOC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                            "                  "                   3-CH.sub.34-Cl                                                                               3-NHCONHC.sub.2 H.sub.5                                                                   CH.sub.2 CH.sub.2 OH                                                                          "                  "                   "             3-NHCOC.sub.6 H.sub.11                                                                    CH.sub.2 CH(CH.sub.3).sub.2                                                                   "                  "                   "             3-NHCOCH.sub.2 CN                                                                         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           "                  "                   "             3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                           CH.sub.2 CH.sub.2 OCOCH.sub.3                                                                 "                  "                   3-CH.sub.34-CN                                                                               3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                            CH.sub.2 CH.sub.2 CONH.sub.2                                                                  "                  "                   3-CH.sub.34-COOC.sub.2 H.sub.5                                                               3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                "                  "                   "             "          CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                         "                  "                   "             "          CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                           "                  "                   "             "          CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                  "                  "                   3-CH.sub.34-SCH.sub.2 CHCH.sub.2                                                             "          CH.sub.2 CH.sub.2 SCH.sub.3                                                                   "                  "                   "             "                                                                                          ##STR36##     CH.sub.2 CH.sub.2 CH.sub.2                                                                        Na.sup.+            "             "                                                                                          ##STR37##     "                  "                   3-CH.sub.34-SO.sub.2 C.sub.2 H.sub.5                                                         3-OC.sub.6 H.sub.5                                                                         ##STR38##     "                  NH.sub.4.sup.+      3-CH.sub.34-SC.sub.6 H.sub.11                                                                3-CH.sub.3 C.sub.6 H.sub.5                                                                               CH.sub.2 CH.sub.2  Na.sup.+            3-CH.sub.34-OC.sub.2 H.sub.5                                                                 "                                                                                          ##STR39##     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)           "                   3-CL4-CN      "          CH.sub.2 CH.sub.2 COOCH.sub.3                                                                 CH.sub.2 CH(C.sub.6 H.sub.5)                                                                      "                   3-CH.sub.34-SCN                                                                              "          CH.sub.2 CH.sub.2 CN                                                                          CH.sub.2 CH(CH.sub.3)                                                                             "                   3-Br4-COOCH.sub.3                                                                            "          C.sub.2 H.sub.5                                                                               CH.sub.2 CH(OH)CH.sub.2                                                                           "                   3-CH.sub.34-COOC.sub.2 H.sub.5                                                               2-CH.sub.3 S                                                                              H              CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   3-CH.sub.34-CONH.sub.2                                                                       3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                      H.sub.5        CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                  "                   3-CH.sub.34-CONHC.sub.2 H.sub.4 OH                                                           "          CH.sub.2 CH(OH)CH.sub.2 Cl                                                                    CH.sub.2 CH.sub.2  "                   3-CH.sub.34-CONHC.sub.4 H.sub.9n                                                             2-OCH.sub.3, 5-CH.sub.3                                                                   C.sub.2 H.sub.5                                                                               "                  "                   3-CH.sub.34-OC.sub.6 H.sub.5                                                                 "          H              CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2           "                   3-CH.sub.34-OC.sub.6 H.sub.4p-CH.sub.3                                                       "          H              "                  "                   3-CH.sub.34-SC.sub.6 H.sub.5                                                                 "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2  K.sup.+             3-CH.sub.34-SCH.sub.2 CH.sub.2 OH                                                            3-CH.sub.3 C.sub.2 H.sub.5                                                                               CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2           "                   3-CH.sub.34-SCH.sub.2 CH.sub.3                                                               "          "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                        "                    ##STR40##    "          "              CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2           "                   3-CH.sub.34-Br                                                                               "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                               "                   "             "          "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2     "                   "             "          "              CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4            "                   "             "          "              CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                    "                   "             "          "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2 CH.sub.2                                                                 "                   3-CH.sub.34-CONH.sub.2                                                                       "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                   3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3                                                    "          "              CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2           "                   3-CH.sub.34-Cl                                                                               "          "              CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                                         "H.sub.2            "             "          "              CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.                                             sub.2 CH.sub.2     "                   "             "          "              CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                   "                   "             "          "              CH.sub.2 CH(Cl)CH.sub.2                                                                           "                   "             "          "              CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4            "                   "             "          "              CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2           "                   "             "          "              CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2           "                   __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________      ##STR41##                                                                     R              (R.sub.1).sub.m                                                                             R.sub.3                                                                           R.sub.4                                                                              Z                M                        __________________________________________________________________________     3-CH.sub.34-Br H            CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               K.sup.+                  "              7-CH.sub.3   "  "     "                "                        "              7-OCH.sub.3  "  "     "                "                        "              7-Cl         "  "     "                "                        "              5-CH.sub.3, 8-OCH.sub.3                                                                     "  "     "                "                        "              5,8-di-OCH.sub.3                                                                            "  "     "                "                        "              5,8-di-CH.sub.3                                                                             "  "     "                "                        "              5-Cl, 8-OCH.sub.3                                                                           "  "     "                "                        "              8-OCH.sub.3  "  "     "                "                        "              8-OC.sub.2 H.sub.5                                                                          H  H     "                "                        "              7-CH.sub.3   "  "     "                "                        3-CH.sub.34-CN 7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                             "                Na.sup.+                 "              7-NHCOH      "  "     "                "                        "              7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "     "                "                        3-CH.sub.34-COOC.sub.2 H.sub.5                                                                7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                   "                "                        "              7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "     "                "                        "              7-NHCOCH.sub.2 Cl                                                                           "  "     "                "                        3-CH.sub.3     7-NHCOC.sub.6 H.sub.5                                                                       "  "     "                "                        "              7-NHCOC.sub.6 H.sub.11                                                                      CH.sub.3                                                                          CH.sub.3                                                                             "                "                        3-CH.sub.34-Cl 7-NHCONHC.sub.2 H.sub.5                                                                     "  "     "                "                        "              7-NHSO.sub.2 CH.sub.3                                                                       "  "     "                "                        "              7-NHCOCH.sub.2 CN                                                                           "  "     "                "                        "              7-NHCOCH.sub.2 OH                                                                           "  "     "                "                        3-Cl4-CN       7-NHCOOC.sub.2 H.sub.5                                                                      "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                      "                        3-Br4-COOCH.sub.3                                                                              ##STR42##   "  "     "                "                        3-CH.sub.34-COOCH.sub.3                                                                       8-OC.sub.4 H.sub.9n                                                                         H  "     CH.sub.2 CH.sub.2                                                                               "                        3-CH.sub.34-CONH.sub.2                                                                        7-CH.sub.3   CH.sub.3                                                                          H     "                "                        3-CH.sub.34-CONHC.sub.2 H.sub.4 OH                                                             ##STR43##   "  CH.sub.3                                                                             "                "                        3-CH.sub.34-CONHC.sub.4 H.sub.9n                                                              7-OC.sub.2 H.sub.5                                                                          "  "     "                "                        3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3                                                     7-OC.sub.4 H.sub.9n                                                                         "  "     "                "                        3-CH.sub.34-COOC.sub.2 H.sub.4 OCH.sub.3                                                      7-CH.sub.3   "  H     "                "                        3-CH.sub.34-SCH.sub.2 CH.sub.2 OH                                                             "            "  "     "                "                        3-CH.sub.34-SCH.sub.2 CH.sub.2 OCOCH.sub.3                                                    "            "  "     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                             "                        3-CH.sub.34-SCH.sub.3                                                                         "            "  "     CH.sub.2 CH.sub.2                                                                               "                        3-CH.sub.34-SO.sub.2 CH.sub.3                                                                 "            "  "     "                "                        3-CH.sub.34-SC.sub.6 H.sub.5                                                                  "            "  "     "                "                        3-CH.sub.34-SC.sub.6 H.sub.4p-C(CH.sub.3).sub.3                                               "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2         K.sup.+                  3-CH.sub.24-SC.sub.6 H.sub.4p-Cl                                                              "            "  "     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                            "                         ##STR44##     "            "  "     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                            "                         ##STR45##     "            "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                         ##STR46##     "            "  "     CH.sub.2 CH(CH.sub.3)                                                                           "                        3-CH.sub.34-SC.sub.6 H.sub.11                                                                 "            "  "     CH.sub.2 CH(OH)CH.sub.2                                                                         "                        3-CH.sub.34-SCN                                                                               "            "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                         "                        3-CH.sub.34-OC.sub.6 H.sub.5                                                                  "            "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)        "                        3-CH.sub.34-OC.sub.2 H.sub.5                                                                  "            "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)         "                        3-CH.sub.34-SCH.sub.2 CHCH.sub.2                                                              "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                        3-CH.sub.34-Br "            "  "     CH.sub. 2 CH.sub.2 CH.sub.2 NHSO.sub.                                          2 CH.sub.2 CH.sub.2                                                                             "                        "              "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                           CH.sub.2        "                        "              "            "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                        "              "            "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2         "                        "              "            "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2         "                        "              "            "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                                   ".sub.4                  "              "            "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4          "                        "              "            "  "     CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                       "                        "              "            "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub                                          .2 CH.sub.2      "                        "              "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub. 5)CH.sub.2 CH.sub.2                                                                      "                        "              "            "  "     CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3                                          )CH.sub.2 CH.sub.2                                                                              "                        __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________      ##STR47##                                                                     R                  (R.sub.1).sub.m                                                                              R.sub.3                                                                            Z                     M                   __________________________________________________________________________     3-CH.sub.34-Cl     6-CH.sub.3    H   CH.sub.2 CH.sub.2     K.sup.+             "                  H             H   "                     "                   "                  "             CH.sub.3                                                                           "                     "                   "                  6-CH.sub.3    "   "                     "                   3-Cl4-CN           "             "   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  "                   "                  6-OCH.sub.3   "   "                     "                   3-CH.sub.3         "             "   CH.sub.2 CH.sub.2     "                   3-CH.sub.34-COOC.sub.2 H.sub.5                                                                    6-CH.sub.3    "   CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                 "                   3-CH.sub.34-CONH.sub.2                                                                            "             "   CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2              "                   3-CH.sub.34-CONHC.sub.2 H.sub.4 OH                                                                "             "   CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                 "                   3-CH.sub.34-CONHC.sub.4 H.sub.9n                                                                  "             "   CH.sub.2 CH(CH.sub.3) "                   3-CH.sub.34-CONHC.sub.3 H.sub.6 OCH.sub.3                                                         "             "   CH.sub.2 CH(C.sub.6 H.sub.5)                                                                         "                   3-CH.sub.34-CO.sub.2 CH.sub.2 H.sub.2 OCH.sub.3                                                   6-OC.sub.2 H.sub.5                                                                           "   CH.sub.2 CH.sub.2     "                   3-CH.sub.34-CONHCH.sub.3                                                                          6-NHCOCH.sub.3                                                                               "   "                     Na.sup.+            3-CH.sub.34-Br     6-NHCOH       "   "                     "                   "                  6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "   "                     "                   "                  6-NHCOCH.sub.2 Cl                                                                            "   "                     "                   "                  6-NHCOCH.sub.2 CN                                                                            "   "                     "                   "                  6-NHCOCH.sub.2 CONH.sub.2                                                                    "   "                     "                   "                  6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "   "                     "                   3-CH.sub.34-SC.sub.2 H.sub.5                                                                      6-NHCOOC.sub.2 H.sub.5                                                                       "   "                     "                   3-CH.sub.34-SCH.sub.2 CH.sub.2 OH                                                                 6-NHCONHC.sub.2 H.sub.5                                                                      "   "                     "                   3-CH.sub.34-SCH.sub.2 CHCH.sub.2                                                                  6-NHCOC.sub.6 H.sub.5                                                                        "   "                     "                   3-CH.sub.34-SCH.sub.2 CH.sub.2 OCOCH.sub.3                                                        6-NHCOC.sub.6 H.sub.11                                                                       "   "                     "                   3-CH.sub.34-SC.sub.6 H.sub.5                                                                      6-NHSO.sub.2 CH.sub.3                                                                        "   "                     "                   3-CH.sub.34-SC.sub.6 H.sub.4p-C(CH.sub.3).sub.2                                                   6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "   "                     "                   3-CH.sub.34-SC.sub.6 H.sub.11                                                                      ##STR48##    "   "                     "                   3-CH.sub.34-SO.sub.2 CH.sub.2 CH.sub.2 OH                                                         6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "   "                     "                   3-CH.sub.34-SO.sub.2 CH.sub.2 CH.sub.3                                                            6-CH.sub.3    "   CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                   3-CH.sub.34-OC.sub.6 H.sub.5                                                                      "             "   CH.sub.2 CH.sub.2     "                   3-CH.sub.34-OC.sub.6 H.sub.4p-OCH.sub.3                                                           "             "   "                     "                    ##STR49##         "             "   "                     "                    ##STR50##         "             "   "                     "                    ##STR51##         "             "   "                     "                   3-CH.sub.34-SCH.sub.2 CH(OH)CH.sub.2 OH                                                           "             "   "                     "                   3-CH.sub.34-SCH.sub.2 COOCH.sub.3                                                                 "             "   "                     "                   3-CH.sub.34-OC.sub.2 H.sub.5                                                                      "             H   CH.sub.2 CH(CH.sub.3) "                   3-CH.sub.34-Br     "             CH.sub.3                                                                           CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                           K.sup.+             "                  "             "   CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                           CH.sub.2             "                   "                  "             "   CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3                                          )CH.sub.2 CH.sub.2 CH.sub.2                                                                          "                   "                  "             "   CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                            "                   "                  "             "   CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                   "                  "             "   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2                                                                         "H.sub.2            "                  "             "   CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4p-CH.sub.3)CH.sub.2 CH.sub.2                                                                  "                   "                  "             "   CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                           "                   "                  "             "   CH.sub.2 CH(Cl)CH.sub.2                                                                              "                   "                  "             "   CH.sub.2 CH(OH)CH.sub.2                                                                              "                   "                  "             "   CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                      "                   "                  "             "   CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)              "                   "                  "             "   CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                     "                   "                  "             "   CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                       "                   "                  "             "   CH.sub.2 CH.sub.2 CONHC.sub.2                                                                        ".sub.4             "                  "             "   CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2              "                   "                  "             "   CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2              "                   "                  "             "   CH.sub.2 CH.sub.2 NHCONHCH.sub.2                                               CH.sub.2              "                   "                  "             "   CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub                                          .2 CH.sub.2           "                   "                  "             "   CH.sub.2 CH.sub.2 N(COC.sub.6                                                  H.sub.5)CH.sub.2 CH.sub.2                                                                            "                   __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR52##                                                                     A      R          (R.sub.1).sub.m                                                                          R.sub.2       Z                M                   __________________________________________________________________________     H      4-CN       2-CH.sub.3                                                                               H             CH.sub.2 CH.sub.2                                                                               K.sup.+             "      "          2-Cl      "             "                "                   "      "          2,5-di-Cl "             "                "                   "      "          2,5-di-CH.sub.3                                                                          "             "                "                   "      "          2,5-di-OCH.sub.3                                                                         "             "                "                   "      "          3-OCH.sub.3                                                                              C.sub.2 H.sub.5                                                                              "                "                   "      "          2-OCH.sub.3,                                                                             H             "                "                                     5-NHCOCH.sub.3                                               "      "          2-CH.sub.3, 3-Cl                                                                         "             "                "                   "      "          2-OCH.sub. 3, 5-Cl                                                                       "             "                "                   "      "          3-NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                              "                "                   "      "          3-NHCOC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.4 OCH.sub.3                                                                    "                "                   "      "          3-NHCOCH.sub.2 OH                                                                        CH.sub.2 C.sub.6 H.sub.5                                                                     "                "                   "      "          3-NHCOCH.sub.2 OCH.sub.3                                                                 C.sub.6 H.sub.11                                                                             "                "                   "      "          3-NHCOC.sub.6 H.sub.5                                                                    CH.sub.2 C.sub.6 H.sub.11                                                                    "                "                   "      "          3-NHCOOC.sub.2 H.sub.5                                                                   CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                           "                "                   "      "          3-NHCONHC.sub.2 H.sub.5                                                                  CH.sub.2 CH.sub.2 OH                                                                         "                "                   C.sub.6 H.sub.5                                                                       3-SC.sub.2 H.sub.54-CN                                                                    3-NHCOC.sub.6 H.sub.11                                                                   CH.sub.2 CH(CH.sub.3).sub.2                                                                  "                "                   "      3-SC.sub.2 H.sub.54-COOCH.sub.3                                                           3-NHCOCH.sub.2 CN                                                                        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          "                "                   "      3-SC.sub.2 H.sub.54-CONH.sub.2                                                            3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                          CH.sub. 2 CH.sub.2 OCOCH.sub.3                                                               "                "                   "      3-SCH.sub.34-CN                                                                           3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                           CH.sub.2 CH.sub.2 CONH.sub.2                                                                 "                "                   "      "          3-CH.sub.3                                                                               CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                               "                "                   "      "          "         CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                        "                "                   "      "          "         CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                          "                "                   SO.sub.2 C.sub.6 H.sub.5                                                              "          "         CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                 "                "                   COCH.sub.3                                                                            4-CN       "         CH.sub.2 CH.sub.2 SCH.sub.3                                                                  "                "                   H      "          "                                                                                         ##STR53##    CH.sub.2 CH.sub.2 CH.sub.2                                                                      Na.sup.+            "      "          "                                                                                         ##STR54##    "                "                   "      "          3-OC.sub. 6 H.sub.5                                                                       ##STR55##    "                NH.sub.4.sup.+      COOC.sub.2 H.sub.5                                                                    "          3-CH.sub.3                                                                               C.sub.6 H.sub.5                                                                              CH.sub.2 CH.sub.2                                                                               Na.sup.+            H      "          "                                                                                         ##STR56##    CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)         "                   CH.sub.3                                                                              4-CN       "         CH.sub.2 CH.sub.2 COOCH.sub.3                                                                CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                   "      4-COOCH.sub.3                                                                             "         CH.sub.2 CH.sub.2 CN                                                                         CH.sub.2 CH(CH.sub.3)                                                                           "                   "      4-CONH.sub.2                                                                              "         C.sub.2 H.sub.5                                                                              CH.sub.2 CH(OH)CH.sub.2                                                                         "                   CH.sub.2 CH.sub.3                                                                     4-CN       2-CH.sub.3 S                                                                             H             CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2         "                   C.sub.6 H.sub.5                                                                       "          3-CH.sub.3                                                                               C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                      H.sub.5       CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                "                   "      4-COOCH.sub.3                                                                             "         CH.sub.2 CH(OH)CH.sub.2 Cl                                                                   CH.sub.2 CH.sub.2                                                                               "                   C.sub.6 H.sub.4p-Cl                                                                   "          2-OCH.sub.3, 5-CH.sub.3                                                                  C.sub.2 H.sub.5                                                                              "                "                   C.sub.6 H.sub.4o-CH.sub.3                                                             "          "         H             CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2         "                   C.sub.6 H.sub.5                                                                       "          "         H             "                "                   "      "          "         "             CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2                                                                               K.sup.+             H      4-CONHC.sub.2 H.sub.4 OH                                                                  3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                              CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2         "                   "      4-CONHC.sub.4 H.sub.9n                                                                    "         "             CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                   "     4-COOC.sub.2 H.sub.4 OCH.sub.3                                                            "         "             CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub. 2 CH.sub.2                                                    CH.sub.2          "                   "      4-CONHC.sub.3 H.sub.6 OCH.sub.3                                                           "         "             CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                             "                   "      4-CN       "         "             CH.sub.2 CH.sub.2 N(COCH.sub.3)C                                               H.sub.2 CH.sub.2 "                   "      "          "         "             CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4          "                   "      "          "         "             CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                   "      "          "         "             CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2         "                   SO.sub.2 CH.sub.3                                                                     4-CN       "         "             CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                    "                   SO.sub.2 C.sub.6 H.sub.5                                                              "          "         "             CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2         "                   SO.sub.2 CH.sub.2 CH.sub.3                                                            "          "         "             CH.sub. 2 CH.sub.2 N(SO.sub.2                                                  C.sub.6 H.sub.11)CH.sub.2                                                      CH.sub.2         "                   H      "          "         "             CH.sub.2 CH.sub.2 N(COCH.sub.3)C                                               H.sub.2 CH.sub.2 "                   "      "          "         "             CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                 "                   "      "          "         "             CH.sub.2 CH(Cl)CH.sub.2                                                                         "                   "      "          "         "             CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4          "                   "      "          "         "             CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2         "                   "      "          "         "             CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2         "                   __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR57##                                                                     A       R            (R.sub.1).sub.m                                                                             R.sub.3                                                                           R.sub.4                                                                              Z                M                  __________________________________________________________________________     H       4-CN        H             CH.sub.3                                                                          CH.sub.3                                                                             CH.sub.2 CH.sub.2                                                                               K.sup.+            "       "           7-CH.sub.3    "  "     "                "                  "       "           7-OCH.sub.3   "  "     "                "                  "       "           7-Cl          "  "     "                "                  "       "           5-CH.sub.3, 8-OCH.sub.3                                                                      "  "     "                "                  "       "           5,8-di-OCH.sub.3                                                                             "  "     "                "                  "       "           5,8-di-CH.sub.3                                                                              "  "     "                "                  "       "           5-Cl, 8-OCH.sub.3                                                                            "  "     "                "                  "       "           8-OCH.sub.3   "  "     "                "                  "       "           8-OC.sub.2 H.sub.5                                                                           H  H     "                "                  "       "           7-CH.sub.3    "  "     "                "                  CH.sub.3                                                                               "           7-NHCOCH.sub.3                                                                               CH.sub.3                                                                          CH.sub.3                                                                             "                Na.sup.+           "       "           7-NHCOH       "  "     "                "                  H       4-COOCH.sub.3                                                                              7-NHCOCH.sub.2 OCH.sub.3                                                                     "  "     "                "                  "       4-COOC.sub.2 H.sub.5                                                                       7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              H  CH(CH.sub.3).sub.2                                                                   "                "                  "       4-COOC.sub.2 H.sub.4 OCH.sub.3                                                             7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                               "  "     "                "                  "       4-CONH.sub.2                                                                               7-NHCOCH.sub.2 Cl                                                                            "  "     "                "                  "       4-CONHC.sub.2 H.sub.5                                                                      7-NHCOC.sub.6 H.sub.5                                                                        "  "     "                "                  "       "           7-NHCOC.sub.6 H.sub.11                                                                       CH.sub.3                                                                          CH.sub.3                                                                             "                "                  "       "           7-NHCONHC.sub.2 H.sub.5                                                                      "  "     "                "                  C.sub.6 H.sub.5                                                                        4-CN        7-NHSO.sub.2 CH.sub.3                                                                        "  "     "                "                  "       "           7-NHCOCH.sub.2 CN                                                                            "  "     "                "                  C.sub.6 H.sub.4p-Cl                                                                    "           7-NHCOCH.sub.2 OH                                                                            "  "     "                "                  C.sub.6 H.sub.4p-CH.sub.3                                                              "           7-NHCOOC.sub.2 H.sub.5                                                                       "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                                      "                  SO.sub.2 CH.sub.3                                                                      "                                                                                           ##STR58##    "  "     "                "                  "       4-COOCH.sub.3                                                                              8-OC.sub.4 H.sub.9n                                                                          H  "     CH.sub.2 CH.sub.2                                                                               "                  SO.sub.2 C.sub.6 H.sub.5                                                               "           7-CH.sub.3    CH.sub.3                                                                          H     "                "                  "       4-CN                                                                                        ##STR59##    "  CH.sub.3                                                                             "                "                  "       4-CONHC.sub.2 H.sub.4 OH                                                                   7-OC.sub.2 H.sub.5                                                                           "  "     "                "                  "       4-COOCH(CH.sub.3).sub.2                                                                    7-OC.sub.4 H.sub.9n                                                                          "  "     "                "                  CH.sub.3                                                                               3-SC.sub.2 H.sub.54-CN                                                                     7-CH.sub.3    "  H     "                "                  C.sub.6 H.sub.5                                                                        "           "             "  "     "                "                  "       3-SC.sub.2 H.sub.54-COOCH.sub.3                                                            "             "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2         "                  "       3-SCH.sub.34-COOC.sub.2 H.sub.5                                                            "             "  "     CH.sub.2 CH.sub.2                                                                               "                  "       3-SO.sub.2 CH.sub.34-COOCH.sub.3                                                           "             "  "     "                "                  "       3-SC.sub.6 H.sub.54-COOCH.sub.3                                                            "             "  "     "                "                  COCH.sub.3                                                                             4-CN        "             "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2                                                                               K.sup.+            "       4-COOCH.sub.3                                                                              "             "  "     CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2         "                  CH.sub.2 CH.sub.2 OH                                                                   "           "             "  "     CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2         "                  H       3-CH.sub.2 CN4-CN                                                                          "             "  "     CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                  "       3-CH.sub.2 CONH.sub.24-CN                                                                  "             "  "     CH.sub.2 CH(CH.sub.3)                                                                           "                  "       4-CN        "             "  "     CH.sub.2 CH(OH)CH.sub.2                                                                         "                  "       "           "             "  "     CH.sub.2 CH(Cl)CH.sub.2                                                                         "                  "       "           "             "  "     CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)        "                  "       "           "             "  "     CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)         "                  "       "           "             "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                      "                  "       "           "             "  "     CH.sub.2 CH.sub.2 CH.sub.2                                                     NHSO.sub.2 CH.sub.2 CH.sub.2                                                                    "                  "       "           "             "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                             "                  "       "           "             "  "     CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                                  "                  "       "           "             "  "     CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                 CH.sub.2        "                  "       "           "             "  "     CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2         "                  "       "           "             "  "     CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4          "                  "       "           "             "  "     CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                 H.sub.4         "                  "       "           "             "  "     CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2         "                  "       "           "             "  "     CH.sub.2 CH.sub.2 N(COCH.sub.3)                                                CH.sub.2 CH.sub.2                                                                               "                  "       "           "             "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5 )CH.sub.2                                                    CH.sub.2         "                  "       "           "             "  "     CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                    "                  __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________      ##STR60##                                                                     A        R            (R.sub.1).sub.m                                                                              R.sub.3                                                                           Z                    M                  __________________________________________________________________________     H        4-CN         6-CH.sub.3    H  CH.sub.2 CH.sub.2    K.sup.+            "        "            H             "  "                    "                  CH.sub.3 "            "             CH.sub.3                                                                          "                    "                  "        4-COOCH.sub.3                                                                               6-CH.sub.3    "  "                    "                  "        4-COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                       "             "  CH.sub.2 CH.sub.2 CH.sub.2                                                                          "H.sub.2           "        4-CONH.sub.2 6-OCH.sub.3   "  "                    "                  "        4-CONHC.sub.2 H.sub.4 OH                                                                    "             "  CH.sub.2 CH.sub.2    "                  "        4-CONHC.sub.3 H.sub.6 OCH.sub.3                                                             6-CH.sub.3    "  CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2             "                  "        4-CONHC.sub.2 H.sub.4 NHCOCH.sub.3                                                          "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2    "                  CH.sub.2 CH.sub.3                                                                       4-CN         "             "  CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2             "                  C.sub.6 H.sub.5                                                                         "            "             "  CH.sub.2 CH(CH.sub.3)                                                                               "                  "        4-COOCH.sub.2 CH.sub.3                                                                      "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                        "                  "        4-CONH.sub.2 6-OC.sub.2 H.sub.5                                                                           "  CH.sub.2 CH.sub.2    "                  C.sub.6 H.sub.4o-Cl                                                                     "            6-NHCOCH.sub.3                                                                               "  "                    Na.sup.+           H        "            6-NHCOH       "  "                    "                  "        4-COOCH.sub.3                                                                               6-NHCOCH.sub.2 CH.sub.2 OCH.sub.3                                                            "  "                    "                  "        "            6-NHCOCH.sub.2 Cl                                                                            "  "                    "                  "        4-CONHC.sub. 4 H.sub.9n                                                                     6-NHCOCH.sub.2 CN                                                                            "  "                    "                  "        "            6-NHCOCH.sub.2 CONH.sub.2                                                                    "  "                    "                  "        "            6-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                              "  "                    "                  SO.sub.2 CH.sub.3                                                                       4-CN         6-NHCOOC.sub.2 H.sub.5                                                                       "  "                    "                  "        4-COOCH.sub.3                                                                               6-NHCONHC.sub.2 H.sub.5                                                                      "  "                    "                  H        3-CH.sub.2 CN4-CN                                                                           6-NHCOC.sub.6 H.sub.5                                                                        "  "                    "                  C.sub.6 H.sub.5                                                                         3-SCH.sub.34-CN                                                                             6-NHCOC.sub.6 H.sub.11                                                                       "  "                    "                  "        3-SCH.sub.2 CH.sub.34-CN                                                                    6-NHSO.sub.2 CH.sub.3                                                                        "  "                    "                  "        3-SCH.sub.2 CH.sub.34-COOCH.sub.3                                                           6-NHCOCH.sub.2 CH.sub.2 OCOCH.sub.3                                                          "  "                    "                  "        3-SCH.sub.34-CONHC.sub.4 H.sub.9n                                                            ##STR61##    "  "                    "                  SO.sub.2 C.sub.6 H.sub.5                                                                4-CN         6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                    "                  "        4-COOCH.sub.3                                                                               6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                          "                  SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3                                                      4-CN         "             "  CH.sub.2 CH.sub.2    "                  SO.sub.2 C.sub.4 H.sub.9n                                                               "            "             "  "                    "                  COCH.sub.3                                                                              "            "             "  "                    "                  COOC.sub.2 H.sub.5                                                                      "            "             "  "                    "                  CH.sub.2 CH.sub.2 OH                                                                    "            "             "  "                    "                  C.sub.6 H.sub.4o-CH.sub.3                                                               "            "             "  "                    "                  "        4-COOCH.sub.3                                                                               "             "  "                    "                  "        4-COOCH(CH.sub.3).sub.2                                                                     "             H  CH.sub.2 CH(CH.sub.3)                                                                               "                  SO.sub.2 C.sub.6 H.sub.11                                                               "            "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                          K.sup.+            H        4-CN         "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2  "                  "        "            "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                   CH.sub.2             "                  "        "            "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                                          "H.sub.2           "        "            "             "  CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.11)CH.sub.2                                                    CH.sub.2             "                  "        "            "             "  CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2 N(SO.sub.2 CH.sub.3)CH.sub                                            .2 CH.sub.2          "                  "        "            "             "  CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.4p-CH.sub.3)CH.sub.2                                             CH.sub.2             "                  "        "            "             "  CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2 CH.sub.2                                                                  "                  C.sub.6 H.sub.5                                                                         "            "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                             "                  "        "            "             "  CH.sub.2 CH(OH)CH.sub.2                                                                             "                  "        "            "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.                                                                       ")                 "        "            "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)             "                  "        "            "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                    "                  "        "            "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                      "                  "        "            "             "  CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4              "                  "        "            "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2             "                  "        "            "             "  CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2             "                  "        "            "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2                                               CH.sub.2             "                  "        "            "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.s                                            ub.2 CH.sub.2        "                  "        "            "             "  CH.sub.2 CH.sub.2 N(COC.sub.6                                                  H.sub.5)CH.sub.2 CH.sub.2                                                                           "                  __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________      ##STR62##                                                                     R                  (R.sub.1).sub.m                                                                           R.sub.2     Z                 M                  __________________________________________________________________________     3,5-di-CN4-CH.sub.3                                                                               2-CH.sub.3 H           CH.sub.2 CH.sub.2 K.sup.+            "                  2-Cl       "           "                 "                  "                  2,5-di-Cl  "           "                 "                  "                  2,5-di-CH.sub.3                                                                           "           "                 "                  3-CN5-C.sub.6 H.sub.5                                                                             2,5-di-OCH.sub.3                                                                          "           "                 "                  3-COOCH.sub.35-C.sub.6 H.sub.5                                                                    3-OCH.sub.3                                                                               C.sub.2 H.sub.5                                                                            "                 "                  3-CONH.sub.25-C.sub.6 H.sub.5                                                                     2-OCH.sub.3, 5-NHCOCH.sub.3                                                               H           "                 "                  3-CONHC.sub.2 H.sub.55-C.sub.6 H.sub.5                                                            2-CH.sub.3, 3-Cl                                                                          "           "                 "                  3-COOCH.sub.3      2-OCH.sub.3, 5-Cl                                                                         "           "                 "                  3-CN               3-NHCOCH.sub.3                                                                            C.sub.2 H.sub.5                                                                            "                 "                  3-CN4-CH.sub.35-COOC.sub.2 H.sub.5                                                                3-NHCOC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 OCH.sub.3                                                                  "                 "                  "                  3-NHCOCH.sub.2 OH                                                                         CH.sub.2 C.sub.6 H.sub.5                                                                   "                 "                  "                  3-NHCOCH.sub.2 OCH.sub.3                                                                  C.sub.6 H.sub.11                                                                           "                 "                  "                  3-NHCOC.sub.6 H.sub.5                                                                     CH.sub.2 C.sub.6 H.sub.11                                                                  "                 "                  3-CN4-CH.sub.35-COCH.sub.3                                                                        3-NHCOOC.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                         "                 "                  3-COOCH.sub.34-CH.sub.35-CN                                                                       3-NHCONHC.sub.2 H.sub.5                                                                   CH.sub.2 CH.sub.2 OH                                                                       "                 "                  3-COOCH.sub.34-CH.sub.35-COC.sub.6 H.sub.5                                                        3-NHCOC.sub.6 H.sub.11                                                                    CH.sub.2 CN(CH.sub.3).sub.2                                                                "                 "                  3-COOCH.sub.35-COC.sub.6 H.sub.5                                                                  3-NHCOCH.sub.2 CN                                                                         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        "                 "                  3-COOCH.sub.35-COCH(CH.sub.3).sub.2                                                               3-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                           CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              "                 "                  "                  3-NHCOCH.sub.2 C.sub.6 H.sub.5                                                            CH.sub.2 CH.sub. 2 CONH.sub.2                                                              "                 "                  "                  3-CH.sub.3 CH.sub.2 CH.sub.2 NHCOCH.sub.3                                                             "                 "                  "                  "          CH.sub.2 CH.sub.2 NHSO.sub.2 CH.sub.3                                                      "                 "                  "                  "          CH.sub.2 CH.sub.2 SO.sub.2 NH.sub.2                                                        "                 "                  "                  "          CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2                                            CH.sub.3    "                 "                  3-SO.sub.2 C.sub.6 H.sub.55-COCH.sub.3                                                            "          CH.sub.2 CH.sub.2 SCH.sub.3                                                                "                 "                  3-SO.sub.2 CH.sub.35-CN                                                                           "                                                                                          ##STR63##  CH.sub.2 CH.sub.2 CH.sub.2                                                                       Na.sup.+           3-SO.sub.2 C.sub.6 H.sub.55-Br                                                                    "                                                                                          ##STR64##  "                 "                  3,5-di-SO.sub.2 CH.sub.3                                                                          3-OC.sub.6 H.sub.5                                                                         ##STR65##  "                 NH .sub.4.sup.                                                                 +                  3,5-di-SO.sub.2 NH.sub.2                                                                          3-CH.sub.3 C.sub.6 H.sub.5                                                                            CH.sub.2 CH.sub.2 Na.sup.+           3,5-di-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                          "                                                                                          ##STR66##  CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)          "                  3-CN5-COCH.sub.3   "          CH.sub.2 CH.sub.2 COOCH.sub.3                                                              CH.sub.2 CH(C.sub.6 H.sub.5)                                                                     "                  3-CN5-COCH(CH.sub.3).sub.2                                                                        "          CH.sub.2 CH.sub.2 CN                                                                       CH.sub.2 CH(CH.sub.3)                                                                            "                  3-CNSCOOC.sub.2 H.sub.5                                                                           "          C.sub.2 H.sub.5                                                                            CH.sub.2 CH(OH)CH.sub.2                                                                          "                  3-CONH.sub.25-COOC.sub.2 H.sub.5                                                                  2-CH.sub.3 S                                                                              H           CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2          "                  3-CONH.sub.25-COCH(CH.sub.3).sub.2                                                                3-CH.sub.3 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.2                                      H.sub.5     CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                 "                  3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2                                                    "           CH.sub.2 CH(OH)CH.sub.2 Cl                                                                CH.sub.2 CH.sub.2 "                  "                  2-OCH.sub.3, 5-CH.sub.3                                                                   C.sub.2 H.sub.5                                                                            "                 "                  "                  "          H           CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2          "                  "                  "          H           "                 "                  "                  "          "           CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2 K.sup.+            3-CONHC.sub.3 H.sub.6 OCH.sub.3SCOCH(CH.sub.3).sub.2                                              3-CH.sub.3 C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2          "                  3-CONHC.sub.4 H.sub.9n-5-COCH(CH.sub.3).sub.2                                                     "          "           CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                       "                  3-CONCHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2                                                   "          "           CH.sub.2 CH.sub.2 NHSO.sub.2                                                   CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2          "                  3-COOCH.sub.35-SO.sub.2 CH.sub.3                                                                  "          "           CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                              "                  3-CONHC.sub.2 H.sub.55-SO.sub.2 CH.sub.3                                                          "          "           CH.sub.2 CH.sub.2 N(COCH.sub.3)C                                               H.sub.2 CH.sub.2  "                  3-CONH.sub.25-SO.sub.2 CH.sub.3                                                                   "          "           CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4           "                  3-CONH.sub.25-SO.sub.2 C.sub.4 H.sub.9n                                                           "          "           CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                   "                  3-COOCH.sub.34-CH.sub.35-SCN                                                                      "          "           CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2          "                  3-CHO4-CH.sub.3    "          "           CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                     "                  3-CONH.sub.25-C.sub.6 H.sub.4p-CH.sub.3                                                           "          "           CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2          "                  3-CN5-COOC.sub.2 H.sub.5                                                                          "          "           CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.11)CH.sub.2                                                      CH.sub.2          "                  3-COOCH.sub.35-COCH(CH.sub.3).sub.2                                                               "          "           CH.sub.2 CH.sub.2 N(COCH.sub.3)C                                               H.sub.2 CH.sub.2  "                  "                  "          "           CH.sub.2 CH(CH.sub.2 OCH.sub.3                                                                   "                  "                  "          "           CH.sub.2 CH(Cl)CH.sub.2                                                                          "                  "                  "          "           CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                H.sub.4           "                  "                  "          "           CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2          "                  "                  "          "           CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2          "                  __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________      ##STR67##                                                                     R                   (R.sub.1).sub.m                                                                             R.sub.3                                                                           R.sub.4                                                                               Z                M                  __________________________________________________________________________     3-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2                                                        H            CH.sub.3                                                                          CH.sub.3                                                                              CH.sub.2 CH.sub.2                                                                               K.sup.+            "                   7-CH.sub.3   "  "      "                "                  3-CONH.sub.25-COCH(CH.sub.3).sub.2                                                                 7-OCH.sub.3  "  "      "                "                  "                   7-Cl         "  "      "                "                  "                   5-CH.sub.3, 8-OCH.sub.3                                                                     "  "      "                "                  "                   5,8-di-OCH.sub.3                                                                            "  "      "                "                  "                   5,8-di-CH.sub.3                                                                             "  "      "                "                  "                   5-Cl, 8-OCH.sub.3                                                                           "  "      "                "                  "                   8-OCH.sub.3  "  "      "                "                  "                   8-OC.sub.2 H.sub.5                                                                          H  H      "                "                  "                   7-CH.sub.3   "  "      "                "                  3-COOCH.sub.35-COCH(CH.sub.3).sub.2                                                                7-NHCOCH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                              "                Na.sup.+           "                   7-NHCOH      "  "      "                "                  "                   7-NHCOCH.sub.2 OCH.sub.3                                                                    "  "      "                "                  "                   7-NHCOCH.sub.2 OC.sub.6 H.sub.5                                                             H  CH(CH.sub.3).sub.2                                                                    "                "                  "                   7-NHCOCH.sub.2 C.sub.6 H.sub.5                                                              "  "      "                "                  3,5-di-CN4-CH.sub.3 7-NHCOCH.sub.2 Cl                                                                           "  "      "                "                  "                   7-NHCOC.sub.6 H.sub.5                                                                       "  "      "                "                  "                   7-NHCOC.sub.6 H.sub.11                                                                      CH.sub.3                                                                          CH.sub.3                                                                              "                "                  "                   7-NHCONHC.sub.2 H.sub.5                                                                     "  "      "                "                  "                   7-NHSO.sub.2 CH.sub.3                                                                       "  "      "                "                  3-CONH.sub.25-C.sub.6 H.sub.5                                                                      7-NHCOCH.sub.2 CN                                                                           "  "      "                "                  "                   7-NHCOCH.sub.2 OH                                                                           "  "      "                "                  3-COOCH.sub.35-C.sub.6 H.sub.5                                                                     7-NHCOOC.sub.2 H.sub.5                                                                      "  "      CH.sub.2 CH.sub.2 CH.sub.2                                                                      "                  3-COOCH.sub.35-COCH.sub.3                                                                           ##STR68##   "  "      "                "                  3-CN5-COOC.sub.2 H.sub.5                                                                           8-OC.sub.4 H.sub.9n                                                                         H  CH.sub.3                                                                              CH.sub.2 CH.sub.2                                                                               "                  3-CN4-CH.sub.35-COOC.sub.2 H.sub.5                                                                 7-CH.sub.3   CH.sub.3                                                                          H      "                "                  3-CN4-CH.sub.35-COCH.sub.3                                                                          ##STR69##   "  CH.sub.3                                                                              "                "                  3-COOCH.sub.34-CH.sub.35-CN                                                                        7-OC.sub.2 H.sub.5                                                                          "  "      "                "                  3-CN4-CH.sub.35-CO.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                        7-OC.sub.4 H.sub.9n                                                                         "  "      "                "                  3-SO.sub.2 C.sub.6 H.sub.5 5-COCH.sub.3                                                            7-CH.sub.3   "  H      "                "                  3-SO.sub.2 C.sub.6 H.sub.4p-Cl 5-COCH.sub.3                                                        "            "  "      "                "                  3-SO.sub.2 CH.sub.35-CN                                                                            "            "  "      CH.sub.2 CH.sub.2 CH.sub.2                                                     CH.sub.2         "                  3-COOCH.sub.35-Br   "            "  "      CH.sub.2 CH.sub.2                                                                               "                  3-COOCH.sub.35-SCN  "            "  "      "                "                  3-CONHC.sub.2 H.sub.4 OH5-COCH(CH.sub.3).sub.2                                                     "            "  "      "                "                  3-CONHC.sub.3 H.sub.6 OCH.sub.35-COCH(CH.sub.3).sub.2                                              "            "  "      CH.sub.2 CH.sub.2 SO.sub.2                                                     CH.sub.2 CH.sub.2                                                                               K.sup.+            3-CN5-SO.sub.2 CH.sub.3                                                                            "            "  "      CH.sub.2 CH.sub.2 OCH.sub.2                                                    CH.sub.2         "                  3,5-di-SO.sub.2 NH.sub.2                                                                           "            "  "      CH.sub.2 CH.sub.2 SCH.sub.2                                                    CH.sub.2         "                  3,5-di-SO.sub.2 NHC.sub.2 H.sub.5                                                                  "            "  "      CH.sub.2 CH(C.sub.6 H.sub.5)                                                                    "                  3-COOCH.sub.35-COC.sub.6 H.sub.5                                                                   "            "  "      CH.sub.2 CH(CH.sub.3)                                                                           "                  3-CONHC.sub.4 H.sub.9n-5-COC.sub.6 H.sub.5                                                         "            "  "      CH.sub.2 CH(OH)CH.sub.2                                                                         "                  3-COOCH.sub.35-SO.sub.2 CH.sub.3                                                                   "            "  "      CH.sub.2 CH(Cl)CH.sub.2                                                                         "                  3-CONHC.sub.2 H.sub.4 OH5-SO.sub.2 CH.sub.3                                                        "            "  "      CH.sub.2 CH(CH.sub.2 OCH.sub.2                                                 CH.sub.3)        "                  3-CHO               "            "  "      CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)                            3-SO.sub.2 C.sub.6 H.sub.5                                                                         "            "  "      CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2          3-CONHC.sub.2 H.sub.55-COCH(CH.sub.3).sub.2                                                        "            "  "      CH.sub.2 CH.sub.2 CH.sub.2                                                     NHSO.sub.2 CH.sub.2 CH.sub.2                                                                    "                  "                   "            "  "      CH.sub.2 CH.sub.2 SO.sub.2                                                     NHCH.sub.2 CH.sub.2                                                                             "                  "                   "            "  "      CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                  "                  "                   "            "  "      CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                 CH.sub.2        "                  "                   "            "  "      CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2         "                  "                   "            "  "      CH.sub.2 CH.sub.2 CONHC.sub.2                                                  H.sub.4          "                  "                   "            "  "      CH.sub.2 CH.sub.2 NHCONHC.sub.2                                                 H.sub.4         "                  "                   "            "  "      CH.sub.2 CH.sub.2 N(SO.sub.2                                                   C.sub.6 H.sub.5)CH.sub.2                                                       CH.sub.2         "                  "                   "            "  "      CH.sub.2 CH.sub.2 N(COCH.sub.3)                                                CH.sub.2 CH.sub.2                                                                               "                  3-COOCH.sub. 34-CH.sub. 35-CONH.sub. 2                                                             "            "  "      CH.sub.2 CH.sub.2 SO.sub.2                                                     N(C.sub.6 H.sub.5)CH.sub.2                                                     CH.sub.2         "                  "                   "            "  "      CH.sub.2 CH.sub.2 SO.sub.2                                                     N(CH.sub.3)CH.sub.2 CH.sub.2                                                                    "                  __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________      ##STR70##                                                                     R                   (R.sub.1).sub.m                                                                              R.sub.3                                                                           Z                      M                  __________________________________________________________________________     3-COOCH.sub. 35-COCH(CH.sub. 3).sub.2                                                              6-CH.sub. 3   H  CH.sub.2 CH.sub.2      K.sup.+            3-CONH.sub. 25-COCH(CH.sub. 3).sub.2                                                               H             H  "                      "                  3-CN 5-COCH(CH.sub. 3).sub.2                                                                       "             CH.sub.3                                                                          "                      "                  "                   6-CH.sub. 3   "  "                      "                  3-CONH.sub. 25-C.sub. 6 H.sub.5                                                                    "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                   "                  "                   6-OCH.sub. 3  "  "                      "                  "                   "             "  CH.sub. 2 CH.sub.2     "                  3-CN 5-C.sub. 6 H.sub.5                                                                            6-CH.sub. 3   "  CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                                                  "                  3-CONHC.sub. 2 H.sub.4 OH5-C.sub. 6 H.sub.5                                                        "             "  CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2                                            CH.sub.2               "                  3-CONHC.sub. 2 H.sub.55-COC.sub. 6 H.sub.5                                                         "             "  CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2                                                                  "                  3-CONHCH.sub. 35-COC.sub. 6 H.sub.5                                                                "             "  CH.sub.2 CH(CH.sub.3)  "                  3-CN 4-CH.sub. 35-COOC.sub. 2 H.sub.5                                                              "             "  CH.sub.2 CH(C.sub.6 H.sub.5)                                                                          "                  3-CN 4-CH.sub. 35-COOC.sub. 2 H.sub.4 OCH.sub.3                                                    6-OC.sub. 2 H.sub.5                                                                          "  CH.sub.2 CH.sub.2      "                  3-CHO 4,5-di-CH.sub. 3                                                                             6-NHCOCH.sub. 3                                                                              "  "                      Na.sup.+           3-CN 4-CH.sub. 35-SCH.sub. 3                                                                       6-NHCOH       "  "                      "                  3-COOCH.sub. 34-CH.sub. 35-CONH.sub. 2                                                             6-NHCOCH.sub. "2 CH.sub.2 OCH.sub.3                                                             "                      "                  3-CONH.sub. 24-CH.sub. 35-CN                                                                       6-NHCOCH.sub. 2 Cl                                                                           "  "                      "                  3,5-di-CN4-CH.sub. 3                                                                               6-NHCOCH.sub. 2 CN                                                                           "  "                      "                  "                   6-NHCOCH.sub. 2 CONH.sub.2                                                                   "  "                      "                  "                   6-NHCOCH.sub. 2 OC.sub.6 H.sub.5                                                             "  "                      "                  "                   6-NHCOOC.sub. 2 H.sub.5                                                                      "  "                      "                  3-CONH.sub. 24-CH.sub. 35-COOCH.sub. 3                                                             6-NHCONHC.sub. 2 H.sub.5                                                                     "  "                      "                  3-SO.sub. 2 CH.sub.35-COCH.sub. 3                                                                  6-NHCOC.sub. 6 H.sub.5                                                                       "  "                      "                  3-SO.sub. 2 C.sub.6 H.sub.55-COCH.sub.3                                                            6-NHCOC.sub. 6 H.sub.11                                                                      "  "                      "                  3-SO.sub. 2 C.sub.6 H.sub.4p-Cl 5-COCH.sub. 3                                                      6-NHSO.sub. 2 CH.sub.3                                                                       "  "                      "                  3-SO.sub. 2 CH.sub.35-Br                                                                           6-NHCOCH.sub. 2 CH.sub.2 OCOCH.sub.3                                                         "  "                      "                  3,5-di-SO.sub. 2 CH.sub.3                                                                           ##STR71##    "  "                      "                  3,5-di-SO.sub. 2 NH.sub.2                                                                          6-NHCOCH.sub.2 CH.sub.2 CH.sub.2 OH                                                          "  "                      "                  3,5-di-SO.sub. 2 NHC.sub.2 H.sub.5                                                                 6-CH.sub.3    "  CH.sub.2 CH.sub.2 CH.sub.2                                                                            "                  3-CONHC.sub. 2 H.sub.4 OH5-COCH(CH.sub. 3).sub.2                                                   "             "  CH.sub.2 CH.sub.2      "                  3-CONHC.sub. 3 H.sub.6 OCH.sub.3 5-COCH(CH.sub.3).sub.2                                            "             "  "                      "                  3-CONHC.sub. 2 H.sub.4 NHCOCH.sub.3                                                                "             "  "                      "                  3-CONHC.sub. 4 H.sub. 9n-5-C.sub.6 H.sub.5                                                         "             "  "                      "                  3-CN 5-COOC.sub.2 H.sub.5                                                                          "             "  "                      "                  3-CN 4-CH.sub.3 5-COOCH(CH.sub.3).sub.2                                                            "             "  "                      "                  3-CN 4-CH.sub.3 5-CONHC.sub.2 H.sub.5                                                              "             "  "                      "                  3-CN 4-CH.sub.3 5-CONHC.sub.6 H.sub.5                                                              "             H   CH.sub.2 CH(CH.sub.3) "                  3-CONH.sub.2 5-SO.sub.2 CH.sub.3                                                                   "             CH.sub.3                                                                          CH.sub.2 CH.sub.2 N(SO.sub.2                                                   CH.sub.3)CH.sub.2 CH.sub.2                                                                            K.sup.+            3-CONH.sub.2 5-COCH(CH.sub.3).sub.2                                                                "             "  CH.sub.2 CH.sub.2 SO.sub.2 NHCH.sub.2                                           CH.sub.2              "                  "                   "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(CH.sub.3                                          )CH.sub.2 CH.sub.2 CH.sub.2                                                                           "                  "                   "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.5)CH.sub.2 CH.sub.2                                                                             "                  "                   "             "  CH.sub.2 CH.sub.2 SO.sub.2 N(C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                  "                   "             "  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            N(SO.sub.2 CH.sub.3)CH.sub.2                                                                          "H.sub.2           "                   "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.4 p-CH.sub.3)CH.sub.2 CH.sub.2                                                                  "                  3-CONHC.sub.2 H.sub.5 5-COCH(CH.sub.3).sub.2                                                       "             "  CH.sub.2 CH.sub.2 N(SO.sub.2 C.sub.6                                           H.sub.11)CH.sub.2 CH.sub.2                                                                            "                  "                   "             "  CH.sub.2 CH(Cl)CH.sub.2                                                                               "                  "                   "             "  CH.sub.2 CH(OH)CH.sub.2                                                                               "                  "                   "             "  CH.sub.2 CH(CH.sub.2 OCH.sub.3)                                                                       "                  "                   "             "  CH.sub.2 CH(CH.sub.2 OC.sub.6                                                  H.sub.5)               "                  "                   "             "  CH.sub.2 CH(OCOCH.sub.3)CH.sub.2                                                                      "                  "                   "             "  CH.sub.2 CH.sub.2 NHCOCH.sub.2                                                                        "                  "                   "             "  CH.sub.2 CH.sub.2 CONHC.sub.2                                                                         ".sub.4            "                   "             "  CH.sub.2 CH.sub.2 NHCOOCH.sub.2                                                CH.sub.2               "                  "                   "             "  CH.sub.2 CH.sub.2 COOCH.sub.2                                                  CH.sub.2               "                  "                   "             "  CH.sub.2 CH.sub.2 NHCONHCH.sub.2                                               CH.sub.2               "                  "                   "             "  CH.sub.2 CH.sub.2 N(COCH.sub.3)CH.sub                                          .2 CH.sub.2            "                  "                   "             "  CH.sub.2 CH.sub.2 N(COC.sub.6                                                  H.sub.5)CH.sub.2 CH.sub.2                                                                             "                  __________________________________________________________________________

EXAMPLES 11-20 Diazotization of 5-Amino-3-ethylthio-1,2,4-thiadiazole

5-Amino-3-ethylthio-1,2,4-thiadiazole (8.05 g., 0.05 m) is diazotized exactly as described in Examples 28-37 and a 0.005 m aliquot coupled to 0.005 m portion of the couplers of Examples 1-10 in the manner previously illustrated.

EXAMPLES 21-30 Diazotization of 5-Amino-3-methyl-4-cyanoisothiazole

To 25 ml of concentrated H₂ SO₄ is added 3.6 g. of NaNO₂ allowing the temperature to rise. The solution is cooled and 50 ml of 1:5 acid is added below 10° C. Stirring is continued and 6.95 g (0.05 m) of 5-amino-3-methyl-4-cyanoisothiazole is added below 5° C., followed by an additional 50 ml of 1:5 acid. After stirring at 0°-5° C. for 2 hrs., a 0.005 m aliquot of the diazonium salt is coupled to 0.005 m of the couplers of Examples 1-10 as previously described to produce rubine to violet dyes for polyamides.

EXAMPLES 41-50 Diazotization of 5-Amino-4-carbomethoxypyrazole

Nitrosyl sulfuric acid is prepared by adding 3.6 g. NaNO₂ to 25 ml of concentrated H₂ SO₄. The solution is cooled and 100 ml of L;5 acid is added below 20° C. After further cooling, 5-amino-4-carbomethoxypyrazole (7.05 g., 0.05 m) is added at 0°-5° C. and stirring continued for 2 hrs. A 0.005 m aliquot of the diazonium solution is coupled to 0.005 m. of the couplers of Examples 1-10 in the manner previously described to produce red dyes for polyamides.

EXAMPLES 51-60 Diazotization of 2-Amino-3-carbomethoxy-5-isobutyrylthiophene

To 150 g. of 60% aqueous acetic acid is added 11.35 g. (0.05 m) of 2-amino-3-carbomethoxy-5-isobutyrylthiophene at room temperature. Ten grams of concentrated onc. H₂ SO₄ is added and the mixture cooled to 0° C. A solution of 3.6 g NaNO₂ in 25 ml of conc. H₂ SO₄ is added below 10° C. and stirring continued for 1 hr. at 0°-5° C. A 0.005 m aliquot of this diazonium salt is coupled to 0.005 m portions of the couplers of Examples 1-10 as previously illustrated to produce violet to reddish-blue dyes for polyamides. 

We claim:
 1. A compound of the formulae D--N═N--Coupler, wherein D is selected from the heterocyclic amines of the formula ##STR72## ring A may bear a substituent selected from lower alkyl, substituted lower alkyl, lower alkoxy, halogen, lower alkylsulfonyl, SO₂ O aryl, SO₂ NH₂, SO₂ NH--lower alkyl, SO₂ N--(dilower alkyl), arylsulfonyl, substituted SO₂ NH--lower alkyl, acylamido, aryl, arylthio, alkenylthio, cyclohexylthio, thiocyano, cyclohexylsulfonyl, lower alkylthio, substituted lower alkylthio and cyclohexyl;ring B may bear a substituent selected from lower alkyl, substituted lower alkyl, aryl, lower alkylthio, cyclohexylthio, substituted lower alkylthio and lower alkylsulfonyl; ring C may bear one or two substituents selected from alkyl, substituted lower alkyl, halogen, cyano, carbamoyl, CONH--lower alkyl, substituted CONH--lower alkyl, lower alkoxycarbonyl, lower alkylthio, substituted lower alkylthio, alkenylthio, arylthio, cyclohexylthio, S-heterocycle, aryloxy, and lower alkoxy; ring D may bear one or two substituents selected from lower alkyl, substituted lower alkyl, lower alkoxycarbonyl, lower alkylthio, aryl, cyano, carbamoyl, lower alkyl carbamoyl, lower alkylcarbonyl, substituted lower alkyl carbamoyl, and lower alkyl sulfonyl; and ring E may be substituted with one to three substituents selected from lower alkyl, substituted lower alkyl, cyano, lower alkoxycarbonyl, acyl, aroyl, lower alkylsulfonyl, arylsulfonyl, carbamoyl, lower alkyl carbamoyl, substituted lower alkyl carbamoyl, aryl, halogen, sulfamoyl, lower alkyl carbamoyl, substituted lower alkyl, sulfamoyl and formyl; and wherein the various alkyl groups may bear one to three substituents selected from hydroxy, lower alkoxy, aryl, aryloxy, cyclohexyl, lower alkylcyclohexyl, acyloxy, lower alkoxy carbonyl, acylamido, lower alkylsulfonamido, succinimido, glutarimido, phthalimido, 2-pyrrolidono, cyano, carbamoyl, lower alkoxy-alkoxy, lower alkylthio, halogen, arylthio, lower alkylsulfonyl and arylsulfonyl; and wherein the various aryl groups may be substituted with one to three substituents selected from lower alkyl, lower alkoxy, halogen, lower alkoxy carbonyl, lower alkyl sulfonyl, and lower alkylthio; and the Coupler is selected from those of the formulae ##STR73## wherein R₁ is selected from hydrogen, lower alkyl, halogen, lower alkoxy, aryloxy, and --NHCO--R₅ or --NHSO₂ --R₅ wherein R₅ is selected from lower alkyl which may be substituted with hydroxy, lower alkoxy, cyano, aryloxy, aryl, halogen, cycloalkyl, lower alkyl carbonyloxy, or carbamoyl; hydrogen; aryl; alkoxy; alkylamine; 2-furyl; R₂ is selected from hydrogen, aryl, cycloalkyl, and lower alkyl which may be substitued --SO₃ M with alkoxy, alkoxyalkoxy, hydrogen, aryloxy, aryl, cycloalkyl, lower alkylcycloalkyl, furyl, NHCOR₅, NHSO₂ R₅, aryloxy, carbamoyl, lower alkyl carbamoyl, lower alkyl substituted carbamoyl, cyano, alkanoyloxy, halogen, alkoxycarbonyl, succinimido, glutarimido, phthalimido, 2-pyrrolidono, sulfamoyl, lower alkyl substituted sulfamoyl, lower alkylsulfonamide, NHSO₂ --aryl, NHCOO--alkyl, NHCONH--alkyl, formamido, alkylsulfonyl, arylsulfonyl, alkylthio, or arylthio; R₂ may in conjunction with R₁ form a 1,2,3,4-tetrahydroquinoline or benzomorpholine derivative; n is 0, 1 or 2; M is Na⁺, K⁺, NH₄ ⁺, or H⁺ ; R₃ and R₄ are each selected from hydrogen or lower alkyl; Z is selected from straight or branched chain lower alkylene, lower alkylene substituted with aryl, aryloxy, alkoxy, halogen, aryloxy or SO₃ M, --CH₂ (CH₂)_(m) X--CH₂ (CH₂)_(p), where m is 1, 2, or 3, p is 0, 1, 2 or 3, and X is O, S, SO₂, ##STR74## and the various aryl groups may be substituted with lower alkyl, lower alkoxy, or halogen.
 2. A compound according to claim 1 where R₁ is selected from hydrogen, lower alkyl, and lower alkoxy; R₂ is selected from hydrogen or lower alkyl; and Z is straight or branched chain lower alkylene.
 3. A compound according to claim 1 having the formula ##STR75##
 4. A compound according to claim 1 having the formula ##STR76##
 5. A compound according to claim 1 having the formula ##STR77##
 6. A compound according to claim 1 having the formula ##STR78##
 7. A compound according to claim 1 having the formula ##STR79##
 8. A compound according to claim 1 having the formula ##STR80##
 9. A compound according to claim 1 having the formula ##STR81##
 10. A compound according to claim 1 having the formula ##STR82##
 11. A compound according to claim 1 having the formula ##STR83##
 12. A compound according to claim 1 having the formula ##STR84## 